6-Benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-(dimethylamino)-4-(1-pyrrolidinylmethyl)phenyl ketone → 6-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-(Dimethylamino)-4-(1-pyrrolidinylmethyl)phenyl Ketone

HRID 1387116Notes

Reaction equation

HRID 1387116 reaction equation
[CH3:1][N:2]([CH3:37])[C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][C:19]=3[S:20][C:21]=2N(C)C)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.[N:38]1([CH2:43][CH2:44][O:45][C:46]2[CH:51]=[CH:50][C:49]([Mg]Br)=[CH:48][CH:47]=2)[CH2:42][CH2:41][CH2:40][CH2:39]1>>[CH3:1][N:2]([CH3:37])[C:3]1[CH:4]=[C:5]([C:15]([C:17]2[C:18]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:25][C:19]=3[S:20][C:21]=2[C:49]2[CH:48]=[CH:47][C:46]([O:45][CH2:44][CH2:43][N:38]3[CH2:39][CH2:40][CH2:41][CH2:42]3)=[CH:51][CH:50]=2)=[O:16])[CH:6]=[CH:7][C:8]=1[CH2:9][N:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 211826356-Benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-(dimethylamino)-4-(1-pyrrolidinylmethyl)phenyl ketoneHCID 178419640HCID 178419640, compound

Product 1

HCID 211827966-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-(Dimethylamino)-4-(1-pyrrolidinylmethyl)phenyl KetoneYield 79%

Procedure

The title compound was prepared in 79% yield by essentially following the procedures outlined in Example 81, Part E, from 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-(dimethylamino)-4-(1-pyrrolidinylmethyl)phenyl ketone (Part F) and 4-[2-(1-pyrrolidinyl)ethoxy]phenyl magnesium bromide (Example 81, Part D).

Sources & evidence

ORD record
ord-a87f84e7817d4d899203f33cfd5a22a8
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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