Triethylamine → 2,2,2-Trichloroethyl 4,4-difluorocyclohexylcarbamate

HRID 2093367Notes

Reaction equation

HRID 2093367 reaction equation
Cl.[F:2][C:3]1([F:10])[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:18](Cl)(=[O:25])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22]>C(Cl)Cl>[F:2][C:3]1([F:10])[CH2:8][CH2:7][CH:6]([NH:9][C:18](=[O:25])[O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 870632,2,2-Trichloroethyl chloroformateHCID 231506694,4-Difluorocyclohexan-1-amine hydrochloride

Product 1

HCID 583592422,2,2-Trichloroethyl 4,4-difluorocyclohexylcarbamateYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Treat a 0° C. mixture of 4,4-difluorocyclohexylamine hydrochloride (3.29 g, 19.2 mmol) and triethylamine (5.88 mL, 42.2 mmol) in CH2Cl2 (192 mL) with 2,2,2-trichloroethyl carbonochloridate (2.91 mL, 21.1 mmol) dropwise. After 1 h, allow the reaction mixture to warm to ambient temperature and stir overnight. Partition the reaction mixture between H2O and CH2Cl2 and separate the layers. Dry the organic layer over Na2SO4, filter, and concentrate under reduced pressure to provide the title compound as an off-white solid (5.75 g, 97%). GC/MS m/z 35Cl 309 (M+).

Workup

  1. additionTreat a 0° C.
  2. customPartition the reaction mixture between H2O and CH2Cl2
  3. customseparate the layers
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-0f3830e833c644e5841672173b4bf956
Source dataset
uspto-grants-2013_05
Patent number
US08445493B2

Reaction notes

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