Hydrazine hydrate (1:1) → N1-(3-Morpholinopropyl)benzene-1,4-diamine
Reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.NN>C(O)C.[Ni].O>[N:1]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 50 °C
Procedure
A suspension of 5.00 gms. of (3-morpholin-4-yl-propyl)-(4-nitro-phenyl)-amine in 110 mL of ethanol is heated to 50° C. Once dissolution is achieved 5.49 mL hydrazine monohydrate is added to the solution. A Raney nickel slurry in water is added to the 50° C. solution dropwise, waiting after each addition for the bubbling to cease. Sufficient quantities of Raney nickel have been added when continued addition of Raney nickel causes no further gas evolution. The reaction is then maintained at 50° C. for an additional hour, and subsequently is cooled to room temperature. The reaction mixture is filtered through a pad of celite (rinsing the pad with methanol). N-(3-Morpholin-4-yl-propyl)-benzene-1,4-diamine (4.39 gms.) is isolated upon evaporation of the filtrate, and is subsequently used without purification in the reaction of Example 297.
Workup
- additionA suspension of 5.00 gms
- dissolutionOnce dissolution
- additionis added to the solution
- waitwaiting
- additionafter each addition for the bubbling
- temperaturesubsequently is cooled to room temperature
- filtrationThe reaction mixture is filtered through a pad of celite (
- washrinsing the pad with methanol)
Sources & evidence
- ORD record
- ord-9381d299fdaa4effa0048ec30dd2d779
- Source dataset
- uspto-grants-2004_07
- Patent number
- US06765012B2
Reaction notes
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