Cyclohexylamine → 3-bromo-N-cyclohexylbenzamide

HRID 2098539Notes

Reaction equation

HRID 2098539 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].C(N(CC)CC)C.[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:24][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:6]

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 8471TriethylamineHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 23063223-bromo-N-cyclohexylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-bromobenzoyl chloride (2.0 g, 9.1 mmol) in CH2Cl2 was added to a solution triethylamine (1.9 ml, 13.7 mmol) and cyclohexylamine (1.15 ml, 10.0 mmol) in CH2Cl2 at room temperature with stirring. After 2 h, the mixture was washed with HCl (4N), brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-bromo-N-cyclohexylbenzamide as a white solid. Yield (2.43 g, 95%): 1H NMR (400 MHz, CD3OD) δ 8.29 (br s, 1H), 7.95 (t, J=2.0 Hz, 1H), 7.42-7.77 (m, 1H), 7.64-7.67 (m, 1H), 7.36 (t, J=8.0 Hz, 1H), 3.78-3.84 (m, 1H), 1.92-1.94 (m, 2H), 1.78-1.81 (m, 2H), 1.65-1.69 (m, 1H), 1.16-1.46 (m, 5H).

Workup

  1. washthe mixture was washed with HCl (4N), brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40b5b76f3d104e9680c4a267b4c4f8cc
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

Loading…