Formic Acid → 4-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzaldehyde
Reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([O:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=1)[CH2:6]2.C(O)=[O:20]>[Ni]>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][CH:5]([O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[O:20])=[CH:13][CH:12]=1)[CH2:6]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
The title compound was synthesized by referring to Chem. Pharm. Bull., 1991, 39, 1440. To a solution of 4-(8-methyl-8-azabicyclo[3.2.1]oct-3-yloxy)benzonitrile (300 mg) in formic acid (5 ml) was added Raney nickel (50% suspension in water) (1 ml), and the solution was stirred for 2 hours at 100° C. After filtration through celite pad and several wash with tetrahydrofuran and methanol, the solvent was evaporated in vacuo, and the resulting residue was neutralized by adding a saturated aqueous solution of sodium bicarbonate. After extraction with chloroform and washing with brine, the solution was dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo to provide the title compound (266 mg).
Workup
- customThe title compound was synthesized
- filtrationAfter filtration through celite pad
- washseveral wash with tetrahydrofuran and methanol
- customthe solvent was evaporated in vacuo
- additionby adding a saturated aqueous solution of sodium bicarbonate
- extractionAfter extraction with chloroform
- washwashing with brine
- dry with materialthe solution was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-040a402d0a88439f884c1f874692cb52
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07960412B2
Reaction notes
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