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

HRID 1978884Notes

Reaction equation

HRID 1978884 reaction equation
[CH:1]1([C:6]([CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH:10]=O)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[Na]>>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:10][CH2:9][CH:8]([C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:7])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 5360545SodiumHCID 222441173-Cyclopentanecarbonyl-3-phenylpropionaldehyde

Product 1

HCID 155240311-(2-Methoxyphenyl)-4-[3-(cyclopentanecarbonyl)-3-(phenyl)propyl]piperazineYield 67%

Procedure

Following the procedures described in the Example 1, Step C, the reaction of 3-cyclopentanecarbonyl-3-phenylpropionaldehyde (1.36 mmol) and 1-(2-methoxyphenyl)piperazine (1.49 mmol) with sodium triacetoxyboranehydride (1.77 mmol) gave pure product 1-(2-methoxyphenyl)-4-[3-(cyclopentanecarbonyl)-3-(phenyl)propyl]piperazine (370 mg) in 67% yield. The dihydrochloric acid salt was prepared as described above.

Sources & evidence

ORD record
ord-e184d069b94f471bbd14af03bef86ee0
Source dataset
uspto-grants-2001_05
Patent number
US06239135B1

Reaction notes

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