2-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amine → Tert-butyl 2-(2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazinecarboxylate

HRID 1504294Notes

Reaction equation

HRID 1504294 reaction equation
[CH3:1][C:2]([NH2:15])([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.ClC(Cl)(Cl)C1O[N:19]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>C(Cl)Cl>[CH3:14][C:2]([NH:15][NH:19][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 1209942-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amineHCID 11139943Tert-butyl 3-(trichloromethyl)oxaziridine-2-carboxylate

Product 1

HCID 89808109Tert-butyl 2-(2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.2 g of 2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-amine was dissolved in 30 mL of methylene chloride and mixed with 5.6 g (21 mmol) of separately prepared t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate under cooling with ice. The reaction solution was stirred at room temperature for 30 minutes, washed with 10% aqueous citric acid, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively and dried over anhydrous sodium sulfate, and methylene chloride was removed under reduced pressure. The resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 100 g, ethyl acetate:hexane) to give 1.38 g of the desired product as a white solid.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with 10% aqueous citric acid, with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
  3. dry with materialdried over anhydrous sodium sulfate, and methylene chloride
  4. customwas removed under reduced pressure
  5. customThe resulting residue was purified by intermediate pressure silica gel column chromatography (silica gel 100 g, ethyl acetate:hexane)

Sources & evidence

ORD record
ord-8d4a54362d5c44198c2cc71536a3f897
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

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