Triethylamine → 4-chloro-N-(4,4-difluoro-cyclohexyl)-butyramide

HRID 1672732Notes

Reaction equation

HRID 1672732 reaction equation
[F:1][C:2]1([F:9])[CH2:7][CH2:6][CH:5]([NH2:8])[CH2:4][CH2:3]1.CCN(CC)CC.[Cl:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:17][CH2:18][CH2:19][CH2:20][C:21]([NH:8][CH:5]1[CH2:6][CH2:7][C:2]([F:9])([F:1])[CH2:3][CH2:4]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 783704-Chlorobutyryl chlorideHCID 3847030(4,4-Difluorocyclohexyl)amine

Product 1

HCID 578785924-chloro-N-(4,4-difluoro-cyclohexyl)-butyramideYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4,4-difluoro-cyclohexylamine (295 mg) and Et3N (0.91 mL) in 22 mL of CH2Cl2, add 4-chloro-butyryl chloride (0.42 g). Allow the resulting mixture to stand at room temp for 4 hr. Remove the organic solvent under vacuum. Dissolve the residue in Et2O. Wash the organic layer with 1N HCl, then brine, and then H2O, and dry over Na2SO4, filter and concentrate. Purify the crude material by chromatography to afford 0.41 g of the title compound: mass spectrum (m/z): 240 (M+1).

Workup

  1. customRemove the organic solvent under vacuum
  2. dissolutionDissolve the residue in Et2O
  3. washWash the organic layer with 1N HCl
  4. dry with materialbrine, and then H2O, and dry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-a470d6ced994437eb690a105ae7d19af
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

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