Methyl 4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-3-nitrobenzoate → Methyl 3-amino-4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-benzoate

HRID 1699237Notes

Reaction equation

HRID 1699237 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=3[N+:26]([O-])=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Rh].C>[NH2:26][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:16]=1[CH2:15][NH:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:13][CH2:12]1)[C:20]([O:22][CH3:23])=[O:21]

Participants

4

Reactant 1

HCID 18321552Methyl 4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-3-nitrobenzoate

Product 1

HCID 18321092Methyl 3-amino-4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-benzoate

Reagents, catalysts & solvents 2

HCID 10080373Rhodium carbonCatalystHCID 887MethanolSolvent

Procedure

A solution of 58.0 g (0.151 mol) of methyl 4-[[[1-(phenylmethyl)-4-piperidinyl]amino]methyl]-3-nitrobenzoate in 800 ml of methanol was hydrogenated in the presence of 10 g of 5% rhodium/charcoal for 7 hours at room temperature. The catalyst was filtered off, the filtrate was evaporated down in vacuo. 50.0 g (93.7% of theory) of colourless crystals were obtained, which were further processed without any more purification.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated down in vacuo
  3. custom50.0 g (93.7% of theory) of colourless crystals were obtained
  4. customwhich were further processed without any more purification

Sources & evidence

ORD record
ord-2ab8ec46b9f4408295a3d0570fa39403
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

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