Water → 1-Ethyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide
Reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.[CH2:19]([Br:21])[CH3:20].O>CN(C)C=O>[BrH:21].[CH2:19]([N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]2)=[N:11]1)[CH3:20]Participants
Procedure
To a stirred suspension of 0.86 g of sodium hydride (50% oil dispersion) in 50 ml of dimethylformamide was added, dropwise, 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 15 ml of hot dimethylformamide. The reaction mixture was stirred at ambient temperature and 1.34 ml of ethyl bromide in 10 ml of dimethylformamide was added, dropwise. The reaction was stirred overnight at ambient temperature and poured into water. The aqueous suspension was extracted with ethyl acetate (2X, 100 ml). The extracts were combined, washed with water, dried over anhydrous magnesium sulfate, and the solvent evaporated in vacuo to yield an oil. The oil was dissolved in a minimum amount of ethanol-ether, and a saturated solution of ether-hydrogen bromide was added. The salt was recrystallized from ethanol-ether to yield 2.4 g (52.8%) of product, mp 240°-242° C.
Workup
- additionwas added
- stirringThe reaction was stirred overnight at ambient temperature
- extractionThe aqueous suspension was extracted with ethyl acetate (2X, 100 ml)
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent evaporated in vacuo
- customto yield an oil
- customThe salt was recrystallized from ethanol-ether
Sources & evidence
- ORD record
- ord-4b91bf40c1804299af84ae5eaf5ce425
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04758668
Reaction notes
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