Hydrochloric Acid → 1-(3-Chloro-4-cyclohexylphenyl)-3-(diethylamino)-1-propanone

HRID 2419007Notes

Reaction equation

HRID 2419007 reaction equation
[ClH:1].[CH2:2]([NH:4][CH2:5][CH3:6])[CH3:3].ClC1[CH:13]([CH2:14][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=O)[CH2:12][CH2:11][CH2:10][CH2:9]1.C=[O:24].Cl.[CH2:26](O)[CH3:27]>>[Cl:1][C:26]1[CH:27]=[C:12]([C:11](=[O:24])[CH2:10][CH2:9][N:4]([CH2:5][CH3:6])[CH2:2][CH3:3])[CH:13]=[CH:14][C:15]=1[CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 712FormaldehydeHCID 10197650Diethylammonium chlorideHCID 569758903-Chloro-4-cyclohexylacetophenone

Product 1

HCID 203167581-(3-Chloro-4-cyclohexylphenyl)-3-(diethylamino)-1-propanoneYield 76.5%

Procedure

54 g of diethylamine hydrochloride, 100 g of 3-chloro-4-cyclohexyl-acetophenone and 15.1 g of paraformaldehyde in 75 ml of absolute ethanol were heated under reflux for 4 hours in the presence of 1.5 ml of 10 N hydrochloric acid. When the reaction was complete, the solvent was evaporated over a water bath under the vacuum produced by a water-jet pump, and the residue was then recrystallized from acetone. 116 g (a yield of 76.5% of theory) of 3-chloro-4-cyclohexyl-1-(3-diethylamino-1-oxo-propyl)-benzene were obtained; the product had a melting point of 156°-158° C (with decomposition).

Workup

  1. customthe solvent was evaporated over a water bath under the vacuum
  2. customproduced by a water-jet pump
  3. customthe residue was then recrystallized from acetone

Sources & evidence

ORD record
ord-0d78a687fb0246c0a8686e63ca04f1e7
Source dataset
uspto-grants-1978_08
Patent number
US04104383

Reaction notes

Loading…