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

HRID 906365Notes

Reaction equation

HRID 906365 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-8e20c1f949974839979497248991738a
Source dataset
uspto-grants-2011_09
Patent number
US08012981B2

Reaction notes

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