Ammonia → HCID 25143769, compound
Reaction equation
[OH-].[K+].[C:3]([CH:5]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:6][C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8])#[N:4].N.[H][H]>CO.[Ni]>[NH2:4][CH2:3][CH:5]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:6][C:7]([N:9]([CH2:12][CH3:13])[CH2:10][CH3:11])=[O:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 30 °C
Procedure
To a solution of potassium hydroxide (19 grams) in methanol (114 ml), 3-cyano-N,N-diethyl-5-methyl hexanamide (9.5 grams) was added followed by ammonia solution (38 ml) and Raney nickel (19 grams). Hydrogen pressure of 4.0 kg/cm2 was applied and the reaction mixture was stirred at 30° C. for 22 hours. The reaction mixture was filtered through a hyflow bed. The solvent was distilled off under reduced pressure at a temperature below 60° C. Water (200 ml) was added to the reaction mixture and pH adjusted to 2 with concentrated hydrochloric acid. The aqueous layer was extracted with dichloromethane. The pH of aqueous layer was adjusted to 8.0, with 50% sodium hydroxide. The aqueous layer was extracted with dichloromethane. The solvent was distilled off completely under atmospheric pressure to obtain the title compound as a residue.
Workup
- filtrationThe reaction mixture was filtered through a hyflow bed
- distillationThe solvent was distilled off under reduced pressure at a temperature below 60° C
- additionWater (200 ml) was added to the reaction mixture
- extractionThe aqueous layer was extracted with dichloromethane
- extractionThe aqueous layer was extracted with dichloromethane
- distillationThe solvent was distilled off completely under atmospheric pressure
Sources & evidence
- ORD record
- ord-c4230f41c26440ed893876a921bc3041
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08168828B2
Reaction notes
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