Ammonium formate → [1-(2-Methoxy-2-methylpropyl)piperidin-4-yl]methylamine
Reaction equation
C([N:8](CC1C=CC=CC=1)[CH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[CH2:12][CH2:11]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.O.[Pd]>[CH3:21][O:20][C:17]([CH3:19])([CH3:18])[CH2:16][N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][NH2:8])[CH2:11][CH2:12]1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a solution of N,N-dibenzyl-N-{[1-(2-methoxy-2-methylpropyl)piperidin-4-yl]methyl}amine (EXAMPLE 4, Step 5, 756 mg, 1.85 mmol) and ammonium formate (583 mg, 9.24 mmol) in methanol (40 mL) and water (15 mL) was added 10% palladium on carbon (185 mg) at ambient temperature. The mixture was heated at 80° C. for 6 h. After cooling, the mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo. The obtained residue was partitioned between dichlorometane and aqueous ammonia. After extraction with dichloromethane, the combined organic extract was dried over magnesium sulfate and concentrated to give 275 mg (66%) of the title compound as a pale yellow oil.
Workup
- temperatureAfter cooling
- filtrationthe mixture was filtered through a pad of Celite
- concentrationthe filtrate was concentrated in vacuo
- customThe obtained residue was partitioned between dichlorometane and aqueous ammonia
- extractionAfter extraction with dichloromethane
- extractionthe combined organic extract
- dry with materialwas dried over magnesium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-7f2533ce49ac4c73a8a1485aeceb8595
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07012080B2
Reaction notes
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