Ethanol → 3-Methyl-3,8-diazabicyclo(3.2.1)octane
Reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][N:11]([CH3:16])[CH2:12]2)C1C=CC=CC=1.C(O)C>[Pd].O>[CH3:16][N:11]1[CH2:12][CH:13]2[NH:8][CH:9]([CH2:15][CH2:14]2)[CH2:10]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 8.2 g (0.038 mole) 8-benzyl-3-methyl-3,8-diazabicyclo[3.2.1]octane in 80 ml absolute ethanol containing 0.11 mole dry hydrogen chloride was hydrogenated in the presence of 1.5 g 10% palladium on charcoal at ambient temperature and pressure for 20 hours. The precipitated hydrochloride salt of the desired product was dissolved by addition of a little water, and, after filtration, the solvent was removed carefully in vacuo. The crystalline residue (6.9 g) was triturated with ethanol-diethyl ether containing dry hydrogen chloride to insure complete formation of the somewhat unstable dihydrochloride salt. Filtration gave 6.0 g (79%) of pure product, melting point 272°-280° C (dec.) with sublimation above 200° C.
Sources & evidence
- ORD record
- ord-a547dfea41a94c81afb0e1377e6b6609
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03951980
Reaction notes
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