Ammonium formate → 1-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate
Reaction equation
C([O-])=O.[NH4+].[C:5]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:11][CH2:10]1)(=[O:7])[CH3:6]>CO.[Pd]>[C:5]([O:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:13][CH2:14]1)(=[O:7])[CH3:6]Participants
Conditions
- Temperature
- 80 °C
Procedure
622 mg of ammonium formate and 525 mg of Pd/C (10%) are added to a solution of 530 mg of 1-[4-nitro-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate in 13 ml of methanol. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel, and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure. The residue is taken up with 20 ml of ethyl acetate, 2 ml of water and 8 ml of a saturated aqueous sodium chloride solution. The two phases are separated and the aqueous phase is washed with 3 times 10 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated. The residue is purified on silica, elution being carried out with dichloromethane/MeOH (95/5), so as to give 190 mg of 1-[4-amino-3-(propan-2-yloxy)phenyl]piperidin-4-yl acetate in the form of a brown oil.
Workup
- filtrationThe mixture is filtered on Clarcel
- washthe Clarcel is rinsed with methanol
- concentrationThe filtrate is concentrated under reduced pressure
- customThe two phases are separated
- washthe aqueous phase is washed with 3 times 10 ml of ethyl acetate
- dry with materialThe combined organic phases are dried over magnesium sulfate
- filtrationfiltered
- customevaporated
- customThe residue is purified on silica, elution
Sources & evidence
- ORD record
- ord-c47ce6e9d8224a469c4eaa4bc7b0984f
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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