Hydrochloric Acid → 1-(1-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene

HRID 1789116Notes

Reaction equation

HRID 1789116 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.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1S.[C:27]([BH3-])#N.[Na+].Cl.[CH:32]([OH:35])([CH3:34])[CH3:33]>C(OCC)C>[OH:35][C:32]1([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])[C:34]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:20][CH2:27][CH2:33]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 24813Phosphorus oxychlorideHCID 80599o-ChlorothiophenolHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 544490061-(1-Hydroxy-1,2,3,4-tetrahydro-1-naphthyl)-3-dimethylamino-1-phenyl-1-propene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

By using a method similar to that described in Example 35, but starting from 3-dimethylaminoacrylophenone (6.1 g), phosphorus oxychloride (3 cc), 2-chlorothiophenol (5 g) and sodium cyanoborohydride (1.3 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., a yellow oil is obtained which is dissolved in isopropanol (20 cc). A 5.6N solution (7.8 cc) of hydrochloric acid gas in ethyl ether is added to this solution. The precipitate formed is separated off by filtration and then recrystallised from isopropanol (20 cc). In this way 3-(2-chlorophenylthio)-1-dimethylamino-3-phenyl-2-propene (Z) hydrochloride (2.5 g) is obtained in the form of a white solid melting at 162° C.

Workup

  1. customafter evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C.
  2. customa yellow oil is obtained which
  3. customThe precipitate formed
  4. customis separated off by filtration
  5. customrecrystallised from isopropanol (20 cc)

Sources & evidence

ORD record
ord-0cce6a139615472cb7594067073fa6a4
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

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