Cyclopropylamine → N-[(5-Chloro-2-isopropylphenyl)methylene]cyclopropanamine
Reaction equation
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:14]([CH3:16])[CH3:15])=[C:10]([CH:13]=1)[CH:11]=O>CO>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:14]([CH3:16])[CH3:15])=[C:10]([CH:11]=[N:4][CH:1]2[CH2:3][CH2:2]2)[CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Cyclopropylamine (39.2 g, 0.69 mol) was added to a solution of 5-chloro-2-isopropylbenzaldehyde (II) (120 g, 0.65 mol, 99.6 GC-% by area) in methanol (1200 ml) and the mixture was stirred at room temperature for 2 hours. The solvent was subsequently removed under reduced pressure and N-[(5-chloro-2-isopropylphenyl)-methylene]cyclopropanamine (144 g, 99.2 GC-% by area, 98.5% of theory) was obtained as a light-yellow oil.
Workup
- customThe solvent was subsequently removed under reduced pressure
Sources & evidence
- ORD record
- ord-ee7a85942f9240e687a201ede8b70806
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09440908B2
Reaction notes
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