1-(2-Chloroethyl)pyrrolidine hydrochloride → 1-[2-[2-Methoxy-4-[[6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl]methyl]phenoxy]ethyl]pyrrolidine

HRID 1387108Notes

Reaction equation

HRID 1387108 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=3)=[C:15]([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)=[CH:29][CH:28]=3)[S:14][C:13]=2[CH:41]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl[CH2:44][CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1>>[CH3:26][O:25][C:20]1[CH:19]=[C:18]([CH2:17][C:16]2[C:12]3[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:41][C:13]=3[S:14][C:15]=2[C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][N:36]3[CH2:37][CH2:38][CH2:39][CH2:40]3)=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]=1[O:24][CH2:44][CH2:45][N:46]1[CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

3

Reactant 2

HCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 183184826-Benzyloxy-3-[(3-methoxy-4-hydroxyphenyl)methyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

Product 1

HCID 211826691-[2-[2-Methoxy-4-[[6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl]methyl]phenoxy]ethyl]pyrrolidineYield 30%

Procedure

The title compound was prepared in 30% yield from 6-benzyloxy-3-[(3-methoxy-4-hydroxyphenyl)methyl]-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (Part E) and 1-(2-chloroethyl)pyrrolidine hydrochloride by a method similar to that outlined in Example 188, Part A.

Sources & evidence

ORD record
ord-140843ee293b4f0c8199972c386f6a3d
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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