Ammonia → 2-(Tetrahydro-2H-pyran-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)ethanamine

HRID 512174Notes

Reaction equation

HRID 512174 reaction equation
[O:1]1[CH2:6][CH2:5][C:4](=[C:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)[C:8]#[N:9])[CH2:3][CH2:2]1.N>CO.[Ni]>[O:1]1[CH2:2][CH2:3][CH:4]([CH:7]([C:10]2[CH:11]=[N:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=2)[CH2:8][NH2:9])[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 867162002-(dihydro-2H-pyran-4(3H)-ylidene)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile

Product 1

HCID 867162012-(Tetrahydro-2H-pyran-4-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)ethanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

2-(Dihydro-2H-pyran-4(3H)-ylidene)-2-(6-(trifluoromethyl)pyridin-3-yl)acetonitrile (1.04 g, 3.88 mmol) was dissolved in methanol (50 mL) and 7 M NH3 in methanol (20 mL) was added. The solution was flushed with Ar. Raney nickel (0.033 g, 0.39 mmol) was added and mixture hydrogenated on a Parr Apparatus at room temperature for 4 hours. Then filtered through a plug of celite and concentrated in vacuo. The crude product was used for the next step without further purification.

Workup

  1. customThe solution was flushed with Ar
  2. filtrationThen filtered through a plug of celite and
  3. concentrationconcentrated in vacuo
  4. customThe crude product was used for the next step without further purification

Sources & evidence

ORD record
ord-ce784105eec3485db6208510dc41d444
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Reaction notes

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