Cyclohexylamine → 2-bromo-N-cyclohexylacetamide

HRID 490172Notes

Reaction equation

HRID 490172 reaction equation
[Br:1][CH2:2][C:3](Cl)=[O:4].[CH:6]1([NH2:12])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>O1CCCC1.CN(C1C=CN=CC=1)C>[Br:1][CH2:2][C:3]([NH:12][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 7965CyclohexylamineHCID 89602Bromoacetyl chloride

Product 1

HCID 2462662-bromo-N-cyclohexylacetamideYield 25%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of bromoacetyl chloride (5.50 mL, 66.9 mmol) in tetrahydrofuran (120 mL) at 0° C. was added a mixture of 4-dimethylaminepyridine (2.80 g, 22.9 mmol) and cyclohexylamine (5.00 mL, 43.7 mmol) in tetrahydrofuran (60 mL). The mixture was warmed to room temperature and stirred an additional 18 hours. The reaction was quenched with water and extracted with dichloromethane. The organic phase was dried (sodium sulfate), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (elution with 10% ethyl acetate:hexanes) to provide of the title compound (25% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.18 (m, 5H), 1.64 (m, 5H), 3.52 (m, 1H), 3.99 (s, 2H), 8.04 (br d, 1H, J=7.1 Hz); MS (DCI/NH3) m/e 237/239 (M+NH4)+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel (elution with 10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-2322baadf42c4b979ee7c4eb0996ba78
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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