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

HRID 1978880Notes

Reaction equation

HRID 1978880 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.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[Na]>>[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N:25]1[CH2:26][CH2:27][N:28]([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][CH2:30]1

Participants

4

Reactant 3

HCID 944591-(2-Pyridyl)piperazineHCID 5360545SodiumHCID 120510643-Cyclohexanecarbonyl-3-phenylpropionaldehyde

Product 1

HCID 155418441-(2-Pyridyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazineYield 78.3%

Procedure

Following the procedures described in the Example 1, Step C, the reaction of 3-cyclohexanecarbonyl-3-phenylpropionaldehyde (1.55 mmol) and 1-(2-pyridyl)piperazine (1.55 mmol) with sodium triacetoxyboranehydride (2.0 mmol) gave pure product 1-(2-pyridyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)propyl]piperazine (475 mg) in 78% yield. The oxalate salt was prepared as described above.

Sources & evidence

ORD record
ord-1058c56890204a238239357f5ae3491c
Source dataset
uspto-grants-2001_05
Patent number
US06239135B1

Reaction notes

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