4-Chlorobenzenesulfonyl chloride → 3-Cyanomethyl-1-(4-chlorophenylsulfonyl)pyrrolidine

HRID 1654498Notes

Reaction equation

HRID 1654498 reaction equation
Cl.[C:2]([CH2:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)#[N:3].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:2]([CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH2:6]1)#[N:3]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 200781392-(Pyrrolidin-3-yl)acetonitrile hydrochloride

Product 1

HCID 200781663-Cyanomethyl-1-(4-chlorophenylsulfonyl)pyrrolidineYield 101.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Acylation, in chloroform, of 36.6 g (0.25 mol) of 3-cyanomethylpyrrolidine hydrochloride with 52.7 g (0.25 mol) of para-chlorophenylsulfonic acid chloride, in the presence of 50.5 g (0.5 mol) of triethylamine makes it possible to obtain 72 g of a solid which is purified by chromatography on silica, Merck 70-230 mesh, using as eluent a dichloromethane/methanol mixture (99/1 v/v).

Sources & evidence

ORD record
ord-f4c3f988f98848919c3a250c3f82252d
Source dataset
uspto-grants-1995_04
Patent number
US05407946

Reaction notes

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