Dichloromethane → 1-(3-(Trifluoromethyl)phenyl)cyclopropanamine

HRID 387625Notes

Reaction equation

HRID 387625 reaction equation
Cl.[F:2][C:3]([F:15])([F:14])[C:4]1[CH:5]=[C:6]([C:10]2([NH2:13])[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+].ClCCl>O>[F:2][C:3]([F:14])([F:15])[C:4]1[CH:5]=[C:6]([C:10]2([NH2:13])[CH2:11][CH2:12]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 684727951-(3-(Trifluoromethyl)phenyl)cyclopropanamine hydrochloride

Product 1

HCID 431465831-(3-(Trifluoromethyl)phenyl)cyclopropanamineYield 104.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Added to a solution of 0.794 g of 1-(3-trifluoromethylphenyl)cyclopropylamine hydrochloride in 20 cm3 of water are 4 cm3 of 1M sodium hydroxide at a temperature close to 20° C. This solution is stirred for 15 min. 40 cm3 of dichloromethane are added and the mixture is stirred for 5 min. The aqueous phase is extracted with 30 cm3 of dichloromethane. The organic phases are combined, dried over magnesium sulfate and concentrated using a rotary evaporator under reduced pressure (5 kPa). 700 mg of 1-(3-trifluoromethylphenyl)cyclopropylamine are obtained, which are dissolved in 12 cm3 of dichloromethane. 1 g of tert-butyl [(1S)-2-(3,5-difluorophenyl)-1-oxiran-2-ylethyl]carbamate and 0.329 g of scandium triflate are added to the solution. The light orange-colored suspension is kept stirring at ambient temperature for 20 h. The reaction mixture is concentrated using a rotary evaporator under reduced pressure (5 kPa). The crude product obtained is purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; flow rate: 50 cm3/min; eluent: 70% cyclohexane/30% ethyl acetate). After concentrating the fractions under reduced pressure, 0.87 g of tert-butyl [(1S,2R)-1-(3,5-difluorobenzyl)-2-hydroxy-3-({1-[3-(trifluoromethyl)phenyl]cyclopropyl}amino)propyl]carbamate is obtained in the form of a white solid.

Workup

  1. customclose to 20° C
  2. stirringthe mixture is stirred for 5 min
  3. extractionThe aqueous phase is extracted with 30 cm3 of dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-e2bb741a38c340ffa67b92c87754ba98
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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