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

HRID 845171Notes

Reaction equation

HRID 845171 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.[CH3:19][C:20]1[CH:25]=[CH:24][C:23](S)=[CH:22][CH:21]=1.C([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:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH2:25][CH2:33]1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 78114-MethylbenzenethiolHCID 24813Phosphorus oxychlorideHCID 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 (5 g), phosphorus oxychloride (2.47 cc), 4-methylthiophenol (3.55 g) and sodium cyanoborohydride (1 g), and after evaporating the organic phase to dryness under reduced pressure (2.7 kPa) at 40° C., an orange oil is obtained which is dissolved in isopropanol (40 cc). A 5.6N solution (7 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 (40 cc). In this way 1-dimethylamino-3-(4-methylphenylthio)-3-phenyl-2-propene (Z) hydrochloride (3.3 g) is obtained in the form of a white solid melting at 197°-198° C.

Workup

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

Sources & evidence

ORD record
ord-c7b4f3d1308e4739be272f1fdc43359f
Source dataset
uspto-grants-1988_07
Patent number
US04755599

Reaction notes

Loading…