Hydrochloric Acid → 2-(1-(Trifluoromethyl)cyclopropyl)ethan-1-amine hydrochloride

HRID 715125Notes

Reaction equation

HRID 715125 reaction equation
B.[F:2][C:3]([F:11])([F:10])[C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1.[ClH:12]>C1COCC1>[ClH:12].[F:2][C:3]([F:11])([F:10])[C:4]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 847630882-(1-(Trifluoromethyl)cyclopropyl)acetonitrile

Product 1

HCID 898137322-(1-(Trifluoromethyl)cyclopropyl)ethan-1-amine hydrochlorideYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Add borane (10 M in dimethylsulfide, 3 mL, 30 mmol) to a solution of 2-(1-(trifluoromethyl)cyclopropyl)acetonitrile (2.2 g, 14.7 mmol) in THF (60 mL), under N2, and heat at 70° C. overnight. Cool to 0° C., add methanolic HCl drop-wise, concentrate to dryness, co-evaporate with MeOH, add EtOAc, collect the solids via filtration and dry to afford the title compound (1.1 g, 40%). 1H NMR (400 MHz, DMSO-d6): δ 8.05 (s, 3H), 2.87 (t, J=8.4 Hz, 2H), 1.90-1.86 (m, 2H), 0.96-0.93 (m, 2H), 0.82-0.81 (m, 2H).

Workup

  1. temperatureCool to 0° C.
  2. concentrationconcentrate to dryness, co-evaporate with MeOH
  3. additionadd EtOAc
  4. customcollect the solids
  5. filtrationvia filtration
  6. customdry

Sources & evidence

ORD record
ord-2754fd7eff864dbd9ed5c984a370836f
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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