Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl- → Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-

HRID 1156028

Reaction equation

HRID 1156028 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1>C(O)C.[Pt]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:5]2([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 3060390Piperidine, 1-methyl-4-(4-nitrophenoxy)-4-phenyl-

Product 1

HCID 3060392Piperidine, 4-(p-aminophenoxy)-1-methyl-4-phenyl-Yield 74.4%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

51 g of 1-methyl-4-(4-nitrophenoxy)-4-phenylpiperidine are dissolved in 1.5 liters of ethanol and are hydrogenated under a hydrogen pressure of 1 atmosphere in the presence of platinum. The catalyst is filtered off, the filtrate is concentrated to 300 ml and crystals (which have separated out) are collected. 34.3 g of the title compound of m.p. 173° to 174° C. are obtained by successive concentration of the filtrate.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to 300 ml and crystals (which
  3. customhave separated out)
  4. customare collected

Sources & evidence

ORD record
ord-8ad115a3f6d441419d4866e6503e5fc5
Source dataset
uspto-grants-1982_06
Patent number
US04333942

Linked notes

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