Hydrochloric Acid → HCID 70457188, compound

HRID 1249205Notes

Reaction equation

HRID 1249205 reaction equation
[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](=O)[CH3:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:15][O:16][CH:17]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[CH2:18][NH2:19].Cl>C1C=CC=CC=1>[ClH:26].[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([NH:19][CH2:18][CH:17]([O:16][CH3:15])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 20225281HCID 20225281, compoundHCID 537760561-{4-[(Propan-2-yl)sulfanyl]phenyl}propan-2-one

Product 1

HCID 70457188HCID 70457188, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-(4-Isopropylthiophenyl)propan-2-one (4.16 g) and 2-methoxy-2-(3-chlorophenyl)ethanamine (3.71 g) in dry benzene (100 ml) was boiled under reflux for two hours in an apparatus incorporating a water trap. The solution was cooled and the solvent removed under reduced pressure. The residue was dissolved in ethanol (80 ml), cooled to less than 10° C. and treated portionwise with sodium borohydride (3.0 g) over 30 minutes. The mixture was stirred for one hour and the solvent removed under reduced pressure. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulphate, filtered and evaporated. Chromatography of the residue on silica gel in 2-4% methanol-dichloromethane gave an oil which was converted to its hydrochloride salt by addition of ethereal hydrogen chloride. Crystallisation from methanol-ethyl acetate-hexane gave the title compound, m.p. 133°-9° C., as a 70:30 mixture of diastereoisomers.

Workup

  1. temperatureunder reflux for two hours in an apparatus
  2. temperatureThe solution was cooled
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethanol (80 ml)
  5. temperaturecooled to less than 10° C.
  6. additiontreated portionwise with sodium borohydride (3.0 g) over 30 minutes
  7. customthe solvent removed under reduced pressure
  8. dissolutionThe residue was dissolved in dichloromethane
  9. washwashed with water
  10. dry with materialdried over magnesium sulphate
  11. filtrationfiltered
  12. customevaporated
  13. customChromatography of the residue on silica gel in 2-4% methanol-dichloromethane gave an oil which
  14. customCrystallisation from methanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-08c6a31eb01f4b9b9ce52c9ec8cdb820
Source dataset
uspto-grants-1986_12
Patent number
US04629737

Reaction notes

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