Acetonitrile → HCID 19877141, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([NH2:7])[CH2:5][CH3:6].[C:8](#N)[CH3:9].[H][H]>[Ni]>[CH3:8][CH:9]1[NH:7][CH:4]([CH2:5][CH3:6])[CH2:3][CH2:2][NH:1]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
Sixty grams of 1,3-diaminopentane (96.7% purity, 0.569 mole), 60 g acetonitrile (1.46 moles) and 1 g of wet Raney® nickel (Raney 2800) catalyst were charged to a 300 ml stainless steel autoclave reactor. The mixture was stirred and heated at 90° C. and 500 psig hydrogen pressure for 6 hours. Capillary GC analysis of the cooled product indicated a 36% conversion of 1,3-diaminopentane and 97.4% yield of 2-methyl-4-ethylhexahydropyrimidine. The reactor was recharged with 25 ml (19.5 g) additional acetonitrile and run at 90° C. and 500 psig for 21 hours. Capillary GC analysis of the mixture indicated a 92.1% conversion of 1,3-diaminopentane and 98% yield of 2-methyl-4-ethylhexahydropyrimidine, b.p. 71° C./20 mm Hg. The structure was confirmed by comparison with a mass spectrum of the hexahydropyrimidine obtained by the condensation of 1,3-diaminopentane and acetaldehyde at 50° C.
Sources & evidence
- ORD record
- ord-17e823ad0ffa44f09eceae05f9e4a938
- Source dataset
- uspto-grants-1992_09
- Patent number
- US05149809
Reaction notes
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