Potassium Hydroxide → 1,1-Dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 883786Notes

Reaction equation

HRID 883786 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].[OH-].[K+]>>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:5][CH2:4][N:3]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([CH3:1])[CH2:7]2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 14797Potassium Hydroxide2×HCID 592621571,1-Dimethylethyl (2R)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 592621641,1-Dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Procedure

The title compound was prepared from 1,1-dimethylethyl (2R)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate (D24) using a method similar to that described for D22 in Description 22 although aqueous 2M KOH solution was used in place of solid KOH and the reaction time was 0.5 h. MS (ES): MH+ 306.2, MNa+ 328.2.

Sources & evidence

ORD record
ord-42183b20b9a14138b3e7e30d58b3d753
Source dataset
uspto-grants-2012_08
Patent number
US08236953B2

Reaction notes

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