1-(2-Methoxyphenyl)piperazine → 2-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine

HRID 890985Notes

Reaction equation

HRID 890985 reaction equation
[CH:1]1([C:7]([CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:10][CH:11]=O)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.[Na]>>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N:27]1[CH2:32][CH2:31][N:30]([CH2:11][CH2:10][CH:9]([C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:8])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5360545SodiumHCID 120510643-Cyclohexanecarbonyl-3-phenylpropionaldehyde

Product 1

HCID 155240262-Methoxyphenyl-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazineYield 79.4%

Procedure

Following the procedures described in the Example 1, Step C, the reaction of 3-cyclohexanecarbonyl-3-phenylpropionaldehyde (1.39 mmol) and 2-methoxyphenylpiperazine (1.39 mmol) with sodium triacetoxyboranehydride (1.80 mmol) gave pure product 1-(2-methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine (464 mg) in 79% yield. The oxalate salt was prepared as described above. m.p.=149-151° C.; MS (m/e): 420 (M+).

Sources & evidence

ORD record
ord-9704d88c87104c62a0114303e3207002
Source dataset
uspto-grants-2006_02
Patent number
US07001908B2

Reaction notes

Loading…