Ammonium formate → 2-Isopropoxy-4-(3-(2-methoxyethyl)-4-methylpiperazin-1-YL)aniline
Reaction equation
C([O-])=O.[NH4+].[CH3:5][O:6][CH2:7][CH2:8][CH:9]1[CH2:14][N:13]([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)[CH2:12][CH2:11][N:10]1[CH3:28]>CO.[Pd]>[CH3:5][O:6][CH2:7][CH2:8][CH:9]1[N:10]([CH3:28])[CH2:11][CH2:12][N:13]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[CH2:14]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
112 mg of ammonium formate and 10 mg of Pd/C (10%) are added to a solution of 100 mg of 2-(2-methoxyethyl)-1-methyl-4-[4-nitro-3-(propan-2-yloxy)phenyl]piperazine in 2 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 10 ml of ethyl acetate and 2 ml of water. The two phases are separated, and the aqueous phase is washed with twice 10 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate, filtered and evaporated, so as to obtain 80 mg of 4-[3-(2-methoxyethyl)-4-methylpiperazin-1-yl]-2-(propan-2-yloxy)aniline 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 twice 10 ml of ethyl acetate
- dry with materialThe combined organic phases are dried over magnesium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-eaf1f8b2383d4f6eaa0c554b3d949b50
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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