1-(3-Chloro-4-cyclohexylphenyl)-3-(diethylamino)-1-propanone → HCID 20316756, compound

HRID 2419008Notes

Reaction equation

HRID 2419008 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:14](=[O:22])[CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[B-].[Na+]>CO.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([OH:22])[CH2:15][CH2:16][N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 203167581-(3-Chloro-4-cyclohexylphenyl)-3-(diethylamino)-1-propanoneHCID 22959485Vertellus2×

Product 1

HCID 20316756HCID 20316756, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10340Sodium CarbonateSolvent

Procedure

116 g of the product of step (a) were suspended in a mixture of 1 liter of methanol and 60 ml of 40% sodium carbonate. 40 g of sodium borohydrate were then added slowly to this suspension, maintaining the temperature below 8° C. After all of the sodium borohydrate had been added, the mixture was left for 12 hours at ambient temperature, after which 1.5 liters of 5% soda solution were added and the mixture was extracted with 700 ml of isopropyl ether. The organic phase was washed with water, dried over sodium sulphate and then evaporated to dryness. 81 g (yield 77% of theory) of 3-chloro-4-cyclohexyl-1-(3-diethylamino-1-hydroxy-propyl)-benzene were obtained in the form of a yellow oil.

Workup

  1. temperaturemaintaining the temperature below 8° C
  2. additionafter which 1.5 liters of 5% soda solution were added
  3. extractionthe mixture was extracted with 700 ml of isopropyl ether
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-e1a77c6c671f4a5d87375d72d34f3534
Source dataset
uspto-grants-1978_08
Patent number
US04104383

Reaction notes

Loading…