Hydrazine hydrate (1:1) → HCID 86698027, compound
Reaction equation
O.NN.[CH3:4][N:5]([CH:25]1[CH2:28][O:27][CH2:26]1)[C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([O:21][CH:22]([CH3:24])[CH3:23])[CH:13]=2)[CH2:7]1>C(O)C.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([N:5]([CH3:4])[CH:25]3[CH2:28][O:27][CH2:26]3)[CH2:7]2)=[CH:13][C:14]=1[O:21][CH:22]([CH3:24])[CH3:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
24 mg of palladium-on-carbon (10%) and then 0.269 ml of hydrazine hydrate are added to a solution of 161 mg of (3R)—N-methyl-1-[4-nitro-3-(propan-2-yloxy)phenyl]-N-(oxetan-3-yl)piperidin-3-amine in 4 ml of ethanol. This mixture is heated at between 85° C./90° C. with magnetic stirring for 1 h 30, then 24 mg of palladium-on-carbon (10%) are added while continuing the refluxing for 2 h. 24 mg of palladium-on-carbon (10%) and 0.269 ml of hydrazine hydrate are again added. The mixture is heated for 1 h at 85° C./90° C., and then allowed to return to ambient temperature and the mixture is filtered through a Whatman AutoCup sintered glass funnel. The filtrate is concentrated under vacuum so as to obtain 136 mg of (3R)-1-[4-amino-3-(propan-2-yloxy)phenyl]-N-methyl-N-(oxetan-3-yl)piperidin-3-amine in the form of an orangey-yellow solid which is used for the subsequent step without further purification.
Workup
- customrefluxing for 2 h
- temperatureThe mixture is heated for 1 h at 85° C./90° C.
- customto return to ambient temperature
- filtrationthe mixture is filtered through a Whatman AutoCup sintered glass funnel
- concentrationThe filtrate is concentrated under vacuum so as
Sources & evidence
- ORD record
- ord-46b7899b819e49ffaedfeec047943b12
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115140B2
Reaction notes
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