Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]2O)[CH2:11][CH2:10]1.C(=O)(O)[O-].[Na+].CCOCC>S(=O)(=O)(O)O.C(O)(=O)C.O>[CH:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:24][CH2:25][C:16]=1[CH2:15][N:12]1[CH2:11][CH2:10][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:14][CH2:13]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
6.0 g of 1,2,3,4-tetrahydro-2-[[4-(2-methoxyphenyl)-1-piperazinyl]methyl]-1-naphthalenol (prepared as described in Example 1) is suspended in 24 ml of 20% sulfuric acid/acetic acid and the mixture is heated on a steam bath for 15 minutes. The reaction mixture is then cooled room temperature, diluted with water (200 ml) and then made alkaline to pH 8 using sodium bicarbonate solution. The alkaline suspension is extracted with two 250 ml portions of methylene chloride and the organic phase is back-washed with water (250 ml), dried over anhydrous sodium sulfate, filtered and concentrated. The syrup obtained solidifies upon addition of a minimal amount of ether to yield 5.6 g of the title compound, melting point 84°-85° C.
Workup
- temperaturethe mixture is heated on a steam bath for 15 minutes
- extractionThe alkaline suspension is extracted with two 250 ml portions of methylene chloride
- washthe organic phase is back-washed with water (250 ml)
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe syrup obtained solidifies
Sources & evidence
- ORD record
- ord-d2b273b9385a4b05a27f1ab9c1177119
- Source dataset
- uspto-grants-1978_12
- Patent number
- US04130646
Linked notes
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