3-(Dimethylamino)-1-phenyl-1-propanone → alpha-(1-Methyl-2-pyrrolidinyl)acetophenone 2,4,6-triisopropylbenzenesulphonylhydrazone hydrochloride
Reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16]([NH:19][N:20]=[C:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28])(=[O:18])=[O:17])([CH3:3])[CH3:2].CN(C)CCC(C1C=CC=CC=1)=O.C(C1C=C(C(C)C)C=C(C(C)C)C=1S(NN)(=O)=O)(C)C.[ClH:68].CN1CCCC1CC(C1C=CC=CC=1)=O>>[ClH:68].[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:11])[CH3:12])[CH:7]=[C:6]([CH:13]([CH3:14])[CH3:15])[C:5]=1[S:16]([NH:19][N:20]=[C:21]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH3:28])(=[O:18])=[O:17])([CH3:2])[CH3:3]Participants
5
Reactant 4
Product 1
Procedure
α-(1-Methyl-2-pyrrolidinyl)acetophenone 2,4,6-triisopropylbenzenesulphonylhydrazone can be prepared by a method similar to that described in Example 22 for the preparation of β-dimethylaminopropiophenone, 2,4,6-triisopropylbenzenesulphonylhydrazone, but starting from 2,4,6-triisopropylbenzenesulphonylhydrazine (30.6 g) and α-(1-methyl-2-pyrrolidinyl)acetophenone hydrochloride (28.3 g). In this way, α-(1-methyl-2-pyrrolidinyl)acetophenone 2,4,6-triisopropylbenzenesulphonylhydrazone hydrochloride (31.1 g) is obtained in the form of a white solid melting at 210° C.
Sources & evidence
- ORD record
- ord-e86a3e9ff2604fdf978a729dc5841fcf
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04686309
Reaction notes
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