Tetrahydrofuran → 5-Chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)aniline

HRID 1258628Notes

Reaction equation

HRID 1258628 reaction equation
[Cl:1][C:2]1[C:9]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([F:19])([F:18])[F:17])[CH2:11]2)=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([N+:20]([O-])=O)[CH:3]=1.C1COCC1>[Pt].CO>[Cl:1][C:2]1[C:9]([N:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([F:19])([F:18])[F:17])[CH2:11]2)=[CH:8][C:5]([NH:6][CH3:7])=[C:4]([CH:3]=1)[NH2:20]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 441206424-chloro-N-methyl-2-nitro-5-(3-(trifluoromethyl)piperidin-1-yl)aniline

Product 1

HCID 679576925-Chloro-2-methylamino-4-(3-(trifluoromethyl)piperidin-1-yl)aniline

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 4-chloro-N-methyl-2-nitro-5-(3-(trifluoromethyl)piperidin-1-yl)aniline (250 mg, 0.7 mmol), THF (6 mL), MeOH (6 mL) and Pt/C (50 mg) was stirred for 4 h at 35° C. under a hydrogen atmosphere (3.2 bar). The catalyst was removed by filtration and the mixture was concentrated to give the sub-title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-71f6b0c2434641a285de8a63bb4fc3f4
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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