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

HRID 592334Notes

Reaction equation

HRID 592334 reaction equation
NC1C=CC(C[N:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=CC=1.Br[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1.N1(C(OC(C)(C)C)=O)CCNCC1>>[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][N:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][CH2:12]2)=[CH:25][CH:26]=1)([O-:32])=[O:31]

Participants

4

Reactant 3

HCID 660114-Nitrobenzyl bromideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 12045001tert-Butyl 4-((4-aminophenyl)methyl)piperazine-1-carboxylate

Product 1

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

Procedure

tert-Butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (G49) can be prepared by the nucleophilic displacement of commercially available 1-(bromomethyl)-4-nitrobenzene (G47) with tert-butyl piperazine-1-carboxylate (G7) to give tert-butyl 4-(4-nitrobenzyl)piperazine-1-carboxylate (G48). Subsequent reduction with hydrogen in the presence of a catalyst, for example 10% palladium on charcoal, gives tert-butyl 4-(4-aminobenzyl)piperazine-1-carboxylate (G49).

Sources & evidence

ORD record
ord-ef469a1fb88a4e2eb7893615c39c8d12
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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