4-Nitrobenzaldehyde → 1-Boc-4-(4-Nitrobenzyl)piperazine

HRID 644701Notes

Reaction equation

HRID 644701 reaction equation
[N+](C1C=CC(C=O)=CC=1)([O-])=O.N1(C(OC(C)(C)C)=O)CCNCC1.C[C@H:26]1[CH2:31][N:30]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[CH2:29][CH2:28][N:27]1[C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43]>>[N+:39]([C:36]1[CH:35]=[CH:34][C:33]([CH2:32][N:30]2[CH2:31][CH2:26][N:27]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH2:28][CH2:29]2)=[CH:38][CH:37]=1)([O-:41])=[O:40]

Participants

4

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 592622041,1-Dimethylethyl (2S)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 235069461-Boc-4-(4-Nitrobenzyl)piperazine

Procedure

The title compound was prepared from 4-nitrobenzaldehyde and 1,1-dimethylethyl 1-piperazinecarboxylate using a method similar to that described for D1 in Description 1A although the product was purified by column chromatography followed by passing through an SCX column eluting with MeOH then 2M NH3 in MeOH. MS (ES+): 266.1, 222.2, no molecular ion (MH+) observed.

Workup

  1. customwas purified by column chromatography
  2. washeluting with MeOH

Sources & evidence

ORD record
ord-55c78fd3b90946c8a3bee5f16d89b4b8
Source dataset
uspto-grants-2010_04
Patent number
US07700599B2

Reaction notes

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