1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile → [1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine

HRID 578868Notes

Reaction equation

HRID 578868 reaction equation
[Cl:1][C:2]1[C:3]([C:15]2([C:18]#[N:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:13])[F:12])[CH:7]=1>CO.N.[Ni]>[Cl:1][C:2]1[C:3]([C:15]2([CH2:18][NH2:19])[CH2:17][CH2:16]2)=[N:4][CH:5]=[C:6]([CH:8]2[CH2:10][CH:9]2[C:11]([F:14])([F:12])[F:13])[CH:7]=1

Participants

5

Reactant 1

HCID 895441591-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile

Product 1

HCID 89544472[1-[3-Chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamineYield 88.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

509 mg of 1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropanecarbonitrile (step 2) was dissolved in 35 ml of methanol containing 2 ml of ammonia (7N in methanol). The solution was hydrogenated over Raney-nickel (flow: 1 mL/min, 50° C., 40 bar). Then the solvent was removed at reduced pressure to give 455 mg of [1-[3-chloro-5-[2-(trifluoromethyl)cyclopropyl]-2-pyridyl]cyclopropyl]methanamine as an orange oil. 1H-NMR (CDCl3): 8.30 ppm (s, 1H), 7.87 ppm (s, 1H), 2.94 ppm (s, 2H), 2.33 ppm (m, 1H), 1.85 ppm (m, 1H), 1.78 ppm (s, 2H, broad), 1.46 ppm (m, 1H), 1.22 ppm (m, 1H), 1.00 ppm (m, 2H), 0.90 ppm (m, 2H).

Workup

  1. customThen the solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-30732926b0794f3aafd0ceb40839e207
Source dataset
uspto-grants-2015_05
Patent number
US09040708B2

Reaction notes

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