Methyl chloroformate → 39076-02-3
Reaction equation
[NH2:1][CH:2]([CH2:4][CH3:5])[CH3:3].Cl[C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:7][NH:1][CH:2]([CH2:4][CH3:5])[CH3:3].[C:7]([NH:1][CH:2]([CH2:4][CH3:5])[CH3:3])([O:9][CH3:10])=[O:8]Participants
Reactant 3
Product 2
Reagents, catalysts & solvents 2
Procedure
N-Methyl-2-aminobutane was prepared from 2-aminobutane (24.7 g, 333 mmol) by reaction with methyl chloroformate (29 mL, 375 mmol) in dichloromethane (700 mL) containing 4-dimethylaminopyridine (4.25 g, 35 mmol) and triethylamine (58.5 mL, 415 mmol). N-carbomethoxy-2-aminobutane was isolated in 100% yield following washing of the reaction solution with water and 0.1N hydrochloric acid, drying of the solvent over sodium sulfate and rotary evaporation of the solvent. An ethereal solution of the product was added dropwise to a stirred suspension of lithium aluminum hydride (19.0 g, 500 mmol) in ether (1 L). After destruction of the aluminum and lithium complexes by careful addition of water (10 mL), 10% sodium hydroxide (10 mL) and water (57 mL), the solids were filtered and the ether was distilled off at atmospheric pressure. The residue was distilled to give 14 g of N-methyl-2-aminobutane as a clear colorless liquid (b.p.=74°-76° C./720 mm).
Sources & evidence
- ORD record
- ord-e21f06425deb45efa18007053317d4ef
- Source dataset
- uspto-grants-1996_04
- Patent number
- US05508311
Reaction notes
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