Methyl chloroformate → [2-(3-Chloro-phenyl)-1-methyl-ethyl]-carbamic acid methyl ester

HRID 2277584Notes

Reaction equation

HRID 2277584 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH2:13][CH:14]([NH2:16])[CH3:15])[CH:10]=[CH:11][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH3:5][O:4][C:2](=[O:3])[NH:16][CH:14]([CH3:15])[CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 20027470m-Chloroamphetamine

Product 1

HCID 86685920[2-(3-Chloro-phenyl)-1-methyl-ethyl]-carbamic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C., methyl chloroformate (0.67 g, 7.1 mmol) was added dropwise to a mixture of 2-(3-chloro-phenyl)-1-methyl-ethylamine (1.0 g, 5.9 mmol) and potassium carbonate (1.63 g, 11.8 mmol) in THF (20 mL). After the addition, the mixture was stirred at room temperature overnight. After filtration and evaporation of the volatiles, the crude product was purified by flash column chromatography (silica gel, 12 g, 50% hexane in dichloromethane) to give the title compound as a white solid (1.2 g, 90%). MS: 228.1 (M+H+).

Workup

  1. additionAfter the addition
  2. filtrationAfter filtration and evaporation of the volatiles
  3. customthe crude product was purified by flash column chromatography (silica gel, 12 g, 50% hexane in dichloromethane)

Sources & evidence

ORD record
ord-09a98024edda4cf28ca9444f163734bd
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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