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

HRID 327781Notes

Reaction equation

HRID 327781 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.[CH3:12][O:13][C:14]1[CH:25]=[CH:24][CH:23]=[CH:22][C:15]=1[O:16][CH:17]1[CH2:21][CH2:20][NH:19][CH2:18]1>CCOCC>[ClH:11].[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:19][CH2:18][CH2:17][CH2:21][N:19]2[CH2:20][CH2:21][CH:17]([O:16][C:15]3[CH:22]=[CH:23][CH:24]=[CH:25][C:14]=3[O:13][CH3:12])[CH2:18]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 144973553-(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-f8453e5efa654357bfd6ec0d295e04f9
Source dataset
uspto-grants-1993_12
Patent number
US05274097

Reaction notes

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