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

HRID 1789112Notes

Reaction equation

HRID 1789112 reaction equation
C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN=[C:21]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])(=O)=O)(C)C.[C:33]1(=[O:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>>[OH:39][C:33]1([C:21]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH2:23][N:24]([CH3:25])[CH3:26])[C:38]2[C:37](=[CH:27][CH:21]=[CH:22][CH:23]=2)[CH2:36][CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 7967CyclohexanoneHCID 86741729beta-Dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone

Product 1

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

Procedure

By using a procedure similar to that described in Example 22 but starting from β-dimethylaminopropiophenone 2,4,6-triisopropylbenzenesulphonylhydrazone (20 g) and from cyclohexanone (5 cc), 1-(1-hydroxy-1-cyclohexyl)-3-dimethylamino-1-phenyl-1-propene (Z) hydrochloride (6 g) is obtained in the form of a white powder melting at 197° C. after recrystallisation from a mixture (50 cc) of isopropanol and isopropyl ether (60/40 by volume).

Sources & evidence

ORD record
ord-dd5c9bc449b941468df29aa629851196
Source dataset
uspto-grants-1987_08
Patent number
US04686309

Reaction notes

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