Methyl chloroformate → [2-(3-Chloro-2-fluoro-phenyl)-ethylamine]-carbamic methyl ester

HRID 2277579Notes

Reaction equation

HRID 2277579 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:13]([O:15][CH3:16])=[O:14].CCN(CC)CC>C(Cl)Cl>[CH3:16][O:15][C:13](=[O:14])[NH2:10].[Cl:1][C:2]1[C:3]([F:11])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 534035832-(3-Chloro-2-fluorophenyl)ethanamine

Product 1

HCID 86685919[2-(3-Chloro-2-fluoro-phenyl)-ethylamine]-carbamic methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-chloro-2-fluoro-phenyl)-ethylamine (1.30 g, 7.9 mmol) in CH2Cl2 (25 mL) was added dropwise methyl chloroformate (1.04 g, 11 mmol) and Et3N at 5° C. with vigorous stirring. The solution was then stirred at room temperature for 1 h. The reaction was poured into ice-water (50 mL) and extracted with CH2Cl2 (2×25 mL). The organic phase was washed with H2O (2×25 mL), dried over Na2SO4, filtered and evaporated to afford the final product without purification (1.78 g, 98%). MS: 232.1 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (2×25 mL)
  2. washThe organic phase was washed with H2O (2×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-099593641a2f46ee85f6794e083081a1
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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