Ammonium formate → 4-(5-Amino-2-methyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1926580Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[C:18]([N+:20]([O-])=O)[CH:17]=[CH:16][C:15]=2[CH3:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=2[CH3:23])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

4-(2-Methyl-5-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.145 g, 0.45 mmol) was dissolved in a mixture of 10 mL of ethanol and 10 mL of water. Ammonium formiate (0.284 g, 0.4 mmol) and 10% Pd/C (0.048 g) were added and the reaction mixture was stirred for 8 h at 40° C. The reaction mixture was then filtered over Celite and the solvent was evaporated to yield 0.064 g of the title compound which was used in subsequent steps without further purification.

Workup

filtrationThe reaction mixture was then filtered over Celite
customthe solvent was evaporated

Sources & evidence

ORD record: ord-31f9098cbef14450a4bdb308d450368a
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183237B2

Reaction notes

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