Ammonia → (3S,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethyl-3,4,5,6-tetrahydropyridin-2-amine

HRID 530289Notes

Reaction equation

HRID 530289 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]2([CH3:19])[NH:13][C:12](=S)[C@:11]([F:16])([CH3:15])[CH2:10][C:9]2([F:18])[F:17])[CH:7]=1.CO.[NH3:23]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:20])=[C:6]([C@@:8]2([CH3:19])[N:13]=[C:12]([NH2:23])[C@:11]([F:16])([CH3:15])[CH2:10][C:9]2([F:18])[F:17])[CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 118307942(3S,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethylpiperidine-2-thione

Product 1

HCID 118307934(3S,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethyl-3,4,5,6-tetrahydropyridin-2-amineYield 100%

Conditions

Temperature
60 °C

Procedure

(3S,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethylpiperidine-2-thione (750 mg, 2.44 mmol) was dissolved in 7M ammonia in methanol (36 ml, 252 mmol). The reaction mixture was stirred in a sealed vial at 60° C. overnight. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure to afford (3S,6R)-6-(5-amino-2-fluorophenyl)-3,5,5-trifluoro-3,6-dimethyl-3,4,5,6-tetrahydropyridin-2-amine (708 mg, 2.448 mmol, 100% yield) as a pale yellow solid that was used in the next reaction without further purification.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0bce1106ebeb4bb3a4f0d8a8185d7df4
Source dataset
uspto-grants-2016_05
Patent number
US09353084B2

Reaction notes

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