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

HRID 522726Notes

Reaction equation

HRID 522726 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([CH2:6][C:7]#[N:8])[CH2:5][CH2:4]1.[ClH:11]>C1COCC1.CSC>[ClH:11].[F:1][C:2]([F:10])([F:9])[C:3]1([CH2:6][CH2:7][NH2:8])[CH2:5][CH2:4]1

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 1068Dimethyl SulfideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Treat a solution of 2-(1-(trifluoromethyl)cyclopropyl)acetonitrile (2.2 g, 14.7 mmol) in THF (60 mL), under N2, with BH3 (10 M in dimethyl sulfide, 3 mL, 30 mmol) and heat at 70° C. overnight. Cool the mixture to 0° C., treat dropwise with methanolic HCl, concentrate to dryness, dissolve in MeOH, re-concentrate and treat the residue with EtOAc. Collect the solids via filtration and dry to afford the title compound (1.1 g, 40% yield). 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. concentrationconcentrate to dryness
  2. dissolutiondissolve in MeOH
  3. concentrationre-concentrate
  4. additiontreat the residue with EtOAc
  5. customCollect the solids
  6. filtrationvia filtration
  7. customdry

Sources & evidence

ORD record
ord-6acdf09eda344f72acf9e21cfd217619
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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