Allyl bromide → (+/-)-3-(alpha-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

HRID 1900266Notes

Reaction equation

HRID 1900266 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:8]=[C:9]([CH:25]=[CH:26][CH:27]=1)[CH:10]([C:12]1[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=1)[C:15]([N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])=[O:16])Cl)(C)(C)C.[CH3:30][C@H:31]1[CH2:36][NH:35][CH2:34][C@@H:33]([CH3:37])[NH:32]1.[CH2:38](Br)[CH:39]=[CH2:40]>>[CH3:30][CH:31]1[NH:32][CH:33]([CH3:37])[CH2:34][N:35]([CH:10]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[C:9]2[CH:25]=[CH:26][CH:27]=[C:7]([OH:6])[CH:8]=2)[CH2:36]1.[CH2:40]([N:32]1[C@@H:33]([CH3:37])[CH2:34][N:35]([CH:10]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)[C:15]([N:17]([CH2:18][CH3:19])[CH2:20][CH3:21])=[O:16])[C:9]2[CH:25]=[CH:26][CH:27]=[C:7]([OH:6])[CH:8]=2)[CH2:36][C@H:31]1[CH3:30])[CH:39]=[CH2:38]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 214803913-(3-((tert-butyldimethyl-silyl)oxy)-alpha-chlorobenzyl)-N,N-diethylbenzamide

Product 2

HCID 21480445(+/-)-3-(alpha-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamideHCID 22865166(+/-)-cis-3-(alpha-(4-allyl-3,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide

Procedure

(±)-3-(α-(3,5-Dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide was prepared from (3-(3-((tert-butyldimethyl-silyl)oxy)-α-chlorobenzyl)-N,N-diethylbenzamide (Example 1, infra) and cis-2,6-dimethylpiperazine according to the methods of Example 1. This material was then alkylated with allyl bromide and deprotected by methods similar to that in Example 4 to give (±)-cis-3-(α-(4-allyl-3,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N -diethylbenzamide.

Sources & evidence

ORD record
ord-9d71278593b4465390afd3c1ac4784e7
Source dataset
uspto-grants-1996_11
Patent number
US05574159

Reaction notes

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