trans-2-Piperidinocyclohexan-1-ol → (+/-)-6-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-[[trans-2-(1-piperidyl)cyclohexyl]oxy]phenyl Ketone

HRID 1387036Notes

Reaction equation

HRID 1387036 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[C:11]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[CH:29][C:12]=3[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:17][CH:16]=2)=[O:9])=[CH:4][C:3]=1[O:41][CH3:42].[N:43]1([C@@H:49]2[CH2:54][CH2:53][CH2:52][CH2:51][C@H:50]2O)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1>>[CH3:42][O:41][C:3]1[CH:4]=[C:5]([C:8]([C:10]2[C:11]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)=[CH:29][C:12]=3[S:13][C:14]=2[C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][CH2:23][N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:19][CH:20]=2)=[O:9])[CH:6]=[CH:7][C:2]=1[O:1][C@@H:50]1[CH2:51][CH2:52][CH2:53][CH2:54][C@H:49]1[N:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

3

Reactant 2

HCID 111310trans-2-Piperidinocyclohexan-1-olHCID 183184716-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-hydroxyphenyl Ketone

Product 1

HCID 18397537(+/-)-6-Benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-Methoxy-4-[[trans-2-(1-piperidyl)cyclohexyl]oxy]phenyl KetoneYield 72%

Procedure

The title compound was prepared in 72% yield by essentially following the procedures outlined in Example 20, Part B, from 6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 4-hydroxy-3-methoxyphenyl ketone (Example 81, Part F) and (±)-trans-2-(1-piperidyl)cyclohexanol (Example 20, Part A).

Sources & evidence

ORD record
ord-16a9177237c24fc087554b81cd0fad9f
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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