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

HRID 1086038Notes

Reaction equation

HRID 1086038 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]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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

6

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)-benzamide

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-amino-5-chloro-N-[2-(diethylamino)-ethyl]-2-hydroxybenzamide hydrochloride (15 g, 47 mmoles) (from Preparation 1A), tetrabutylammonium bromide (15 g, 47 mmoles), anhydrous potassium carbonate (34.32 g, 0.234 mole), 2-chlorocyclohexanone (8.9 g, 67 mmoles) in DMF (60 ml) was stirred for 4 days. The reaction mixture was partitioned between water and ethyl acetate. The ethyl acetate solution was washed with 0.4N NaOH, water and extracted with 1N HCl (50 ml). The acid extract was basified with saturated sodium carbonate solution and extracted with methylene chloride. The extract was dried and filtered through silica, the filtrate was concentrated and the concentrate diluted with pentane. The oiled-out material solidified on standing and was crystallized from toluene (30 ml) to yield the title compound, mp. 96°-99°.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe ethyl acetate solution was washed with 0.4N NaOH, water
  3. extractionextracted with 1N HCl (50 ml)
  4. extractionThe acid extract
  5. extractionextracted with methylene chloride
  6. customThe extract was dried
  7. filtrationfiltered through silica
  8. concentrationthe filtrate was concentrated
  9. additionthe concentrate diluted with pentane
  10. customwas crystallized from toluene (30 ml)

Sources & evidence

ORD record
ord-acc479b385094eaf8f14768ae4a00d19
Source dataset
uspto-grants-1991_04
Patent number
US05011992

Reaction notes

Loading…