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Revision as of 12:13, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,054 edits Saving copy of the {{chembox}} taken from revid 455805431 of page Pyrrolidine for the Chem/Drugbox validation project (updated: '').  Latest revision as of 14:40, 29 June 2023 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,924 editsm Reverted edit by 112.118.46.47 (talk) to last version by LeyoTag: Rollback 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Watchedfields = changed
| verifiedrevid = 417949770 | verifiedrevid = 464377817
|ImageFileL1=Pyrrolidine.png | ImageFileL1=Pyrrolidine_svg.svg
|ImageSizeL1=80px | ImageSizeL1=80px
|ImageFileR1=Pyrrolidine3d.png | ImageFileR1=Pyrrolidine3d.png
| PIN = Pyrrolidine<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=142 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref>
|ImageSizeR1=100px
| OtherNames=Azolidine<br />Azacyclopentane<br />Tetrahydropyrrole<br />Prolamine<br />Azolane
|IUPACName=Pyrrolidine
⚫ |Section1={{Chembox Identifiers
|OtherNames=azolidine, azacyclopentane, tetrahydropyrrole
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ |Section1= {{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 29008 | ChemSpiderID = 29008
| InChI = 1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2 | InChI = 1/C4H9N/c1-2-4-5-3-1/h5H,1-4H2
Line 21: Line 19:
| StdInChIKey = RWRDLPDLKQPQOW-UHFFFAOYSA-N | StdInChIKey = RWRDLPDLKQPQOW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=123-75-1 | CASNo = 123-75-1
| PubChem=31268 | PubChem = 31268
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LJU5627FYV | UNII = LJU5627FYV
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 33135 | ChEBI = 33135
| SMILES=C1CCNC1 | SMILES = C1CCNC1
| RTECS=UX9650000 | RTECS = UX9650000
| Beilstein = 102395
| Gmelin = 1704
| UNNumber = 1922
| EC_number = 204-648-7
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=4|H=9|N=1 | C=4 | H=9 | N=1
| Appearance=Clear liquid | Appearance=Clear colorless liquid
| Density=0.866 g/cm<sup>3</sup> | Density=0.866 g/cm<sup>3</sup>
| MeltingPtC=-63 | MeltingPtC=-63
| BoilingPtC=87 | BoilingPtC=87
| Solubility=Miscible | Solubility=Miscible
| RefractIndex = 1.4402 at 28°C
| pKa = 11.27 (p''K''<sub>a</sub> of conjugate acid in water),<ref>Hall, H.K., ''J. Am. Chem. Soc.'', '''1957''', ''79'', 5441. DOI: </ref><br />
| MagSus = -54.8·10<sup>−6</sup> cm<sup>3</sup>/mol
⚫ 19.56 (p''K''<sub>a</sub> of conjugate acid in acetonitrile)<ref>Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I.A. Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to Full Span of 28 pKa Units: Unification of Different Basicity Scales. ''J. Org. Chem.'' '''2005''', ''70'', 1019-1028. DOI: </ref>
| pKa = 11.27 (p''K''<sub>a</sub> of conjugate acid in water),<ref>{{Cite journal | last1 = Hall | first1 = H. K. | title = Correlation of the Base Strengths of Amines | doi = 10.1021/ja01577a030 | journal = Journal of the American Chemical Society | volume = 79 | issue = 20 | pages = 5441–5444 | year = 1957 }}</ref><br />
⚫ 19.56 (p''K''<sub>a</sub> of conjugate acid in acetonitrile)<ref>{{Cite journal | last1 = Kaljurand | first1 = I. | last2 = Kütt | first2 = A. | last3 = Sooväli | first3 = L. | last4 = Rodima | first4 = T. | last5 = Mäemets | first5 = V. | last6 = Leito | first6 = I. | last7 = Koppel | first7 = I. A. | doi = 10.1021/jo048252w | title = Extension of the Self-Consistent Spectrophotometric Basicity Scale in Acetonitrile to a Full Span of 28 pKa Units: Unification of Different Basicity Scales | journal = The Journal of Organic Chemistry | volume = 70 | issue = 3 | pages = 1019–1028 | year = 2005 | pmid = 15675863}}</ref>
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| ExternalSDS =
| MainHazards=highly flammable, harmful, corrosive, mutagen | MainHazards=highly flammable, harmful, corrosive, possible mutagen
| FlashPt=3 °C
| FlashPtC = 3
| Autoignition = 345 °C
| NFPA-H = 3 | AutoignitionPtC = 345
| NFPA-F = 3 | NFPA-H = 3
| NFPA-R = 1 | NFPA-F = 3
| NFPA-R = 1
| RPhrases={{R11}} {{R20/21/22}} {{R35}}
| SPhrases={{S16}} {{S26}} {{S28}} {{S36/37}} {{S45}} | GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|302|314|332}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|280|301+312|301+330+331|303+361+353|304+312|304+340|305+351+338|310|312|321|330|363|370+378|403+235|405|501}}
}} }}
| Section8 = {{Chembox Related |Section8={{Chembox Related
| Function = Nitrogen heterocyclic compounds | OtherFunction_label = nitrogen heterocyclic compounds
| OtherFunctn = ] (aromatic with two double bonds)<br />] (one double bond)<br />] (two pentagonal rings) | OtherFunction = ] (aromatic with two double bonds)<br />] (one double bond)<br />] (two pentagonal rings)
}} }}
}} }}

'''Pyrrolidine''', also known as '''tetrahydropyrrole''', is an ] with the molecular formula (CH<sub>2</sub>)<sub>4</sub>NH. It is a cyclic secondary ], also classified as a saturated ]. It is a colourless liquid that is miscible with water and most organic solvents. It has a characteristic odor that has been described as "ammoniacal, fishy, shellfish-like".<ref> {{Webarchive|url=https://web.archive.org/web/20171121194519/http://www.thegoodscentscompany.com/data/rw1009391.html |date=2017-11-21 }}, The Good Scents Company</ref> In addition to pyrrolidine itself, many substituted pyrrolidines are known.

==Production and synthesis==
===Industrial production===
Pyrrolidine is prepared industrially by the reaction of ] and ] at a temperature of 165–200&nbsp;°C and a pressure of 17–21&nbsp;MPa in the presence of a ] and ] catalyst, which is supported on ].<ref name="production">{{cite web |last1=Bou Chedid |first1=Roland |last2=Melder |first2=Johann-Peter |last3=Dostalek |first3=Roman |last4=Pastre |first4=Jörg |last5=Tan |first5=Aik Meam |title=Process for the preparation of pyrrolidine |url=https://patents.google.com/patent/EP2872494B1/en |website=Google Patents |publisher=BASF SE |access-date=5 July 2019 |archive-date=5 July 2019 |archive-url=https://web.archive.org/web/20190705134726/https://patents.google.com/patent/EP2872494B1/en |url-status=live }}</ref>

:]

The reaction is carried out in the liquid phase in a continuous tube- or tube bundle reactor, which is operated in the cycle gas method. The catalyst is arranged as a fixed-bed and the conversion is carried out in the downflow mode. The product is obtained after multistage purification and separation by ] and ].<ref name="production" />

===Laboratory synthesis===
In the laboratory, pyrrolidine was usually synthesised by treating 4-chlorobutan-1-amine with a strong base:

:]
Furthermore, 5-membered ''N''-heterocyclic ring of the pyrrolidine derivatives can be synthesized via ]s.<ref name="R1">{{cite journal |last1=Łowicki |first1=Daniel |last2=Przybylski |first2=Piotr |title=Tandem construction of biological relevant aliphatic 5-membered N-heterocycles |journal=] |date=2022 |volume=235 |pages=114303 |doi=10.1016/j.ejmech.2022.114303|pmid=35344904|s2cid=247580048 }}</ref>

==Occurrence==
Many modifications of pyrrolidine are found in natural and synthetic drugs and drug candidates.<ref name="R1"></ref> The pyrrolidine ring structure is present in numerous natural ]s ''i.a.'' ] and ]. It is found in many drugs such as ] and ]. It also forms the basis for the ] compounds (''e.g.'' ], ]). The ]s ] and ] are, in a structural sense, derivatives of pyrrolidine.
:]
{{clear left}}

==Reactions==
Pyrrolidine is a base. Its basicity is typical of other dialkyl amines.<ref>{{cite journal|title=Correlation of the Base Strengths of Amines|author=H. K. Hall Jr. |journal=J. Am. Chem. Soc.|year=1957|volume=79|issue=20|page=5441|doi=10.1021/ja01577a030}}</ref> Relative to many secondary amines, pyrrolidine is distinctive because of its compactness, a consequence of its cyclic structure.

Pyrrolidine is used as a building block in the synthesis of more complex organic compounds. It is used to activate ]s and ]s toward nucleophilic addition by formation of ]s (e.g. used in the ]):<ref>{{OrgSynth|author=], I. J. Pachter, and M. L. Scheinbaum |year=1974|title=2,2-(Trimethylenedithio)cyclohexanone |volume=54| pages=39|collvol=6|collvolpages=1014|prep=CV6P1014}}</ref>
:]

==References==
<references/>

==External links==
*{{Commonscat-inline}}

]
]
Misplaced Pages:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Pyrrolidine: Difference between pages Add topic