Potassium Carbonate → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-cyclohexyloxy)-benzamide

HRID 1382954Notes

Reaction equation

HRID 1382954 reaction equation
Cl.[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[O:8])=[C:5]([OH:20])[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][C:29]1=[O:34]>CN(C=O)C>[NH2:2][C:3]1[C:18]([Cl:19])=[CH:17][C:6]([C:7]([NH:9][CH2:10][CH2:11][N:12]([CH2:13][CH3:14])[CH2:15][CH3:16])=[O:8])=[C:5]([O:20][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][C:29]2=[O:34])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 132032-ChlorocyclohexanoneHCID 141168774-amino-5-chloro-N-(2-(diethylamino)ethyl)-2-hydroxybenzamide hydrochloride

Product 1

HCID 141168914-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(2-oxo-cyclohexyloxy)-benzamideYield 13.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide hydrochloride (6.4 g, 20 mmoles) and potassium carbonate (13.8 g, 0.1 mole) in DMF (34 ml) and 2-chlorocyclohexanone (3.8 g, 28.6 mmoles) was stirred for 4 days, followed by partition between water and methylene chloride. The organic phase was washed well with water, dried and concentrated. The residue was chromatographed on deactivated silica using methylene chloride (100), methanol (4), ammonia (0.5) as the solvent system. The appropriate fractions were combined and further purified by low pressure liquid chromatography to give 1.0 g of the title compound as a colorless foam. The NMR spectrum (90 MHz) in CDCl3 gave the following resonances: δ8.4 (bs, 1H); 8.16 (s 1H); 6.14 (s, 1H); 4.7 (m, 1H); 4.3 (s, 2H); 3.56 (q, J=7.2 Hz, 2H); 2.62 (m, 6H); 2.3-1.4 (m, 8H); 1.04 (t, J=7.2 Hz, 6H).

Workup

  1. customby partition between water and methylene chloride
  2. washThe organic phase was washed well with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on deactivated silica
  6. customfurther purified by low pressure liquid chromatography

Sources & evidence

ORD record
ord-e1ce9ce775be47c19c6943d816470636
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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