4-Nitrobenzaldehyde → (3R,5S)-1-[(4-Nitrophenyl)methyl]-3,5-dimethylpiperazine

Reaction equation

[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][C@@H:13]1[CH2:18][NH:17][CH2:16][C@H:15]([CH3:19])[NH:14]1>>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:17]2[CH2:16][C@H:15]([CH3:19])[NH:14][C@H:13]([CH3:12])[CH2:18]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 5414-Nitrobenzaldehyde

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

Product 1

HCID 59262210(3R,5S)-1-[(4-Nitrophenyl)methyl]-3,5-dimethylpiperazine

Procedure

The title compound was prepared from 4-nitrobenzaldehyde and (2R,6S)-2,6-dimethylpiperazine using a method similar to that described for D21 in Description 21A. MS (ES): MH+ 250.2.

Sources & evidence

ORD record: ord-73ef899a68064cc9989b9d5bfba359ea
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236953B2

Reaction notes

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