4-methoxy-2-nitro-N-(1-phenylmethyl-4-piperidinyl)-benzylamine → 2-amino-4-methoxy-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

HRID 2217275Notes

Reaction equation

HRID 2217275 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:10]2)=[C:5]([N+:24]([O-])=O)[CH:4]=1>CO>[NH2:24][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:23]=[CH:22][C:6]=1[CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 179586954-methoxy-2-nitro-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

Product 1

HCID 179586822-amino-4-methoxy-N-(1-phenylmethyl-4-piperidinyl)-benzylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3.2 g (9.003 mmol) of 4-methoxy-2-nitro-N-(1-phenylmethyl-4-piperidinyl)-benzylamine in 30 mL methanol was hydrogenated in the presence of 1 g of 10% rhodium charcoal for 5 hours at ambient temperature. The catalyst was filtered off and the filtrate was evaporated down in vacuo. 2.5 g (85% of theoretical) of a colorless, highly viscous oil was obtained, which was further processed without purification. Rf=0.34 (MP F). IR (KBr): no C═O; MS: M+=325.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down in vacuo
  3. custom2.5 g (85% of theoretical) of a colorless, highly viscous oil was obtained
  4. customwhich was further processed without purification

Sources & evidence

ORD record
ord-276e0c6e1433439bab6b0fb0b753f549
Source dataset
uspto-grants-2008_08
Patent number
US07407963B2

Reaction notes

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