Hydrochloric Acid → 1-(3-Aminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine dihydrochloride
Reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]4C(=O)C5=CC=CC=C5C4=O)[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.O.NN.O.[ClH:35]>CO.C(O)C>[ClH:35].[ClH:35].[NH2:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:29]=[CH:30][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of N-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propyl]phthalimide (8.5 g, 21 mmol), hydrazine monohydrate (1.5 g, 30 mmol) in methanol (60 ml) was heated at reflux for 2 hours. At the end of the reaction, methanol was removed to leave a crude solid. To this was added water (60 ml), then the mixture was acidified with HCl to pH 1. The insolubles were filtered with the aid of a pad of Celite. The aqueous solution was basified with 50% NaOH, (pH 13), then extracted with dichloromethane. The combined dichloromethane solution was washed with brine, then dried to a colorless oil (4.5 g). The analytical sample (1.5 g) was prepared by treating the oil with HCl in ethanol at 0° C. The 1-(3-aminopropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine dihydrochloride was obtained as white crystals, 2.03 g, m.p.=231°-234° C.
Workup
- temperaturewas heated
- temperatureat reflux for 2 hours
- customwas removed
- customto leave a crude solid
- filtrationThe insolubles were filtered with the aid of a pad of Celite
- extractionextracted with dichloromethane
- washThe combined dichloromethane solution was washed with brine
- dry with materialdried to a colorless oil (4.5 g)
- customThe analytical sample (1.5 g) was prepared
Sources & evidence
- ORD record
- ord-cc0b3267b7fe4271bf04a3d6ad3486d4
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05854263
Reaction notes
Loading…