Formaldehyde → 5H-Dibenz(b,f)azepine, 10,11-dihydro-2-((4-methyl-1-piperazinyl)methyl)-
Reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[CH2:23]=O>ClC(Cl)C.C(O)(=O)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:2]2[CH:3]=[CH:4][C:5]3[NH:6][C:7]4[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=4[CH2:9][CH2:10][C:11]=3[CH:1]=2)[CH2:19][CH2:18]1Participants
6
Procedure
10,11-Dihydro-5H-dibenz [b,f]azepine (250 g) was suspended in a mixture of 600 ml of dichloroethane and 600 ml of acetic acid, and 155 ml of 1-methylpiperazine was added dropwise to the suspension. To the mixture was added 42 g of paraformaldehyde at 50° C. followed by stirring for 6 hours. The solvent was distilled off under reduced pressure and the residue was diluted with ethyl acetate. The solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to give the product (91%). The obtained product was subjected to the subsequent reaction without particular purification.
Workup
- additionwas added dropwise to the suspension
- distillationThe solvent was distilled off under reduced pressure
- additionthe residue was diluted with ethyl acetate
- washThe solution was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-cf011155c84141b59138b5163e9ca8dd
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378701
Reaction notes
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