N-(1-methyl-4-piperidyl)-7-nitro-benzo[1,3]dioxole-4-carboxamide → 7-amino-N-(1-methyl-4-piperidyl)benzo[1,3]dioxole-4-carboxamide

HRID 2234490Notes

Reaction equation

HRID 2234490 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([C:11]2[C:19]3[O:18][CH2:17][O:16][C:15]=3[C:14]([N+:20]([O-])=O)=[CH:13][CH:12]=2)=[O:10])[CH2:4][CH2:3]1>CO>[NH2:20][C:14]1[C:15]2[O:16][CH2:17][O:18][C:19]=2[C:11]([C:9]([NH:8][CH:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[O:10])=[CH:12][CH:13]=1

Participants

3

Reactant 1

HCID 68682205N-(1-methyl-4-piperidyl)-7-nitro-benzo[1,3]dioxole-4-carboxamide2×

Product 1

HCID 686813937-amino-N-(1-methyl-4-piperidyl)benzo[1,3]dioxole-4-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(1-methyl-4-piperidyl)-7-nitro-benzo[1,3]dioxole-4-carboxamide (Intermediate 224; 290 mg, 0.94 mmol) was suspended in methanol (50 mL) and the system purged with nitrogen. 10% Pd/C (30 mg) was added and the mixture stirred under a hydrogen atmosphere for 2 hours. The catalyst was filtered off and the filtrate evaporated to give the title compound as a white solid (249 mg, 96%).

Workup

  1. customthe system purged with nitrogen
  2. addition10% Pd/C (30 mg) was added
  3. filtrationThe catalyst was filtered off
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-011a93a20bca4638b72e87552454e2e1
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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