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.C[C@H]1CN(CC2C=CC([N+]([O-])=O)=CC=2)CCN1C(OC(C)(C)C)=O>>[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 3

HCID 5414-Nitrobenzaldehyde

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

HCID 592622041,1-Dimethylethyl (2S)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate

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 D1 in Description 1A. MS (ES): MH+ 250.2

Sources & evidence

ORD record: ord-6c9b5b1fef6b4944b1eae2f231cb6279
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853218B2

Reaction notes

Loading…