Ammonium formate → HCID 68467096, compound

HRID 132925

Reaction equation

HRID 132925 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+].CC(C)=O.C(Cl)Cl>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]([Cl:23])=[CH:16][CH:17]=[CH:18][C:19]=2[NH2:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 587677041-Boc-4-(2-chloro-6-nitrophenyl)piperazine

Product 1

HCID 68467096HCID 68467096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 342 mg (1 mmol) of 4-(2-chloro-6-nitro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester in 5.0 mL of MeOH was treated with 630 mg (10 mmol, 10 eq) of ammonium formate and a catalytic amount of 10% Pd—C (34 mg). The reaction mixture was stirred at 65° C. for 30 min. The reaction mixture was then filtered through a pad of celite and concentrated to obtain a yellow solid. TLC (silica, 5% acetone/CH2Cl2): Rf=0.40. MS (electrospray): exact mass calculated for C15H22ClN3O2, 311.14; m/z found, 312.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. concentrationconcentrated
  3. customto obtain a yellow solid

Sources & evidence

ORD record
ord-a0500cb5a08642e4a47fcd628ad2a8d0
Source dataset
uspto-grants-2008_06
Patent number
US07388011B2

Linked notes

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