Ethyl 4-(piperazin-1-yl)benzoate → 4-[4-[[2-(4-Chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-YL]methyl]-1-piperazinyl]benzoic acid ethyl ester

HRID 1920476Notes

Reaction equation

HRID 1920476 reaction equation
O/C=C1/C(=O)CCC(C)(C)C/1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH2:24][CH2:23][C:22]([CH3:26])([CH3:25])[CH2:21][C:20]=2[CH:27]=O)=[CH:15][CH:14]=1.[N:29]1([C:35]2[CH:45]=[CH:44][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:37][CH:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH2:24][CH2:23][C:22]([CH3:25])([CH3:26])[CH2:21][C:20]=2[CH2:27][N:32]2[CH2:31][CH2:30][N:29]([C:35]3[CH:36]=[CH:37][C:38]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:44][CH:45]=3)[CH2:34][CH2:33]2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 2761178Ethyl 4-(piperazin-1-yl)benzoateHCID 12173050(2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanoneHCID 445943302-(4-chlorophenyl)-5,5-dimethyl-1-Cyclohexene-1-carboxaldehyde

Product 1

HCID 251404834-[4-[[2-(4-Chlorophenyl)-5,5-dimethyl-1-cyclohexen-1-YL]methyl]-1-piperazinyl]benzoic acid ethyl ester

Procedure

Scheme 1 shows three synthetic routes used to prepare the aldehyde intermediate (2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-ene-1-carbaldehyde) (4) from (2E)-2-(hydroxymethylene)-4,4-dimethylcyclohexanone (1A). The aldehyde intermediate (4) can then be reacted with ethyl 4-(piperazin-1-yl)benzoate (4A) to provide ethyl 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoate, which is hydrolyzed to provide 4-(4-((2-(4-chlorophenyl)-5,5-dimethylcyclohex-1-en-1-yl)methyl)piperazin-1-yl)benzoic acid (6).

Sources & evidence

ORD record
ord-5967341f19b746adae77cdaa1c666964
Source dataset
uspto-grants-2012_05
Patent number
US08168784B2

Reaction notes

Loading…