4-Fluorobenzenesulfonyl chloride → 1-[3-(4-Fluorophenyl)sulphonamido-propyl]-3-(2-methoxyphenoxy)-pyrrolidine hydrochloride

HRID 2247992Notes

Reaction equation

HRID 2247992 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([Cl:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH2:17]1>CCOCC>[ClH:11].[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][CH2:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:17]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 156240381-(3-Aminopropyl)-3-(2-methoxyphenoxy)-pyrrolidine

Product 1

HCID 156240401-[3-(4-Fluorophenyl)sulphonamido-propyl]-3-(2-methoxyphenoxy)-pyrrolidine hydrochlorideYield 62%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

0.78 g (4.0 mmol) of 4-fluorophenylsulphonyl chloride in 15 ml of ether were added dropwise to a solution of 1.0 g (4.0 mmol) of 1-(3-aminopropyl)-3-(2-methoxyphenoxy)-pyrrolidine in 20 ml of anhydrous ether at 0° C. After 2 hours at room temperature, the mixture was freed from solvent in vacuo and the remaining oily residue was brought to crystallization by trituration with diethyl ether/hexane. In this manner, 1.1 g (62%) of title compound were obtained as a slightly reddish, hygroscopic solid. It melted from 50° C.

Workup

  1. customthe remaining oily residue was brought to crystallization by trituration with diethyl ether/hexane

Sources & evidence

ORD record
ord-d0a7f744eae340bb82a6b3249e33c281
Source dataset
uspto-grants-1991_08
Patent number
US05037841

Reaction notes

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