Hydrochloric Acid → 1-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

HRID 1789103Notes

Reaction equation

HRID 1789103 reaction equation
[CH3:1][N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.P(Cl)(Cl)(Cl)=O.Br[C:20]1[CH:25]=[CH:24][C:23](S)=[CH:22][CH:21]=1.[C:27]([BH3-])#N.[Na+].[OH-:31].[Na+].Cl>C(Cl)(Cl)Cl.C(O)C.CCOCC>[CH:20]1([CH:27]([OH:31])[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH2:3][N:2]([CH3:13])[CH3:1])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 660494-BromothiophenolHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 538458471-Cyclohexyl-4-dimethylamino-2-phenyl-2-buten-1-ol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (5 g), phosphorus oxychloride (2.47 cc), 4-bromothiophenol (5.39 g) and sodium cyanoborohydride (1 g), a chestnut-coloured residue is obtained which is taken up in chloroform. The solution is made alkaline to pH 10 with an aqueous solution of sodium hydroxide. After separation of the chloroform phase, the aqueous phase is extracted with methylene chloride. The organic phases are collected, dried over sodium sulphate, filtered and then evaporated to dryness under reduced pressure (2.7 kPa) at 30° C. A residue is obtained which is dissolved in ethanol (60 cc). A 3N ether solution (7.7 cc) of hydrochloric acid gas is added to this solution. The white solid which precipitates is separated off by filtration and recrystallised from a mixture of isopropanol and methanol (60/40 by volume). In this way 3-(4-bromophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (1.8 g) is obtained in the form of a white solid melting at 252° C.

Workup

  1. customa chestnut-coloured residue is obtained which
  2. customAfter separation of the chloroform phase
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. customThe organic phases are collected
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (2.7 kPa) at 30° C
  8. customA residue is obtained which
  9. customThe white solid which precipitates
  10. customis separated off by filtration
  11. customrecrystallised from a mixture of isopropanol and methanol (60/40 by volume)

Sources & evidence

ORD record
ord-437d9ff9e7c043fe95a9f0b8da7e0249
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

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