Ethyl chloroformate → HCID 21243401, compound

HRID 2309019Notes

Reaction equation

HRID 2309019 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=1)C.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27]>C1(C)C=CC=CC=1>[C:26]([N:2]([CH2:4][CH:5]([CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][CH:9]=1)[CH3:1])([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 13653935N,N-dimethyl-2-benzyl-3-(4-trifluoromethylphenoxy)propylamine

Product 1

HCID 21243401HCID 21243401, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of N,N-dimethyl-2-benzyl-3-(4-trifluoromethylphenoxy)propylamine (22.0 g) and ethyl chloroformate (34.1 g, 30.0 ml) in dry toluene (200 ml) is refluxed for 72 hours. The reaction mixture is cooled to room temperature, and the solvent removed under reduced pressure. Water (200 ml) is added, and the mixture extracted with dichloromethane (2×150 ml). The combined dichloromethane extracts are washed with 2N hydrochloric acid (200 ml) and water (200 ml), and dried over magnesium sulfate. The solvent is removed under reduced pressure to give N-carbethoxy-N-methyl-2-benzyl-3-(4-trifluoromethylphenoxy)propylamine as an oil, which is used without purification for the next synthetic step above.

Workup

  1. customthe solvent removed under reduced pressure
  2. additionWater (200 ml) is added
  3. extractionthe mixture extracted with dichloromethane (2×150 ml)
  4. washThe combined dichloromethane extracts are washed with 2N hydrochloric acid (200 ml) and water (200 ml)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e433051f00394a1fb5cbf66ff6e44d10
Source dataset
uspto-grants-1987_09
Patent number
US04692469

Reaction notes

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