Cyclopropylamine → Benzenemethanamine, 5-​chloro-​N-​cyclopropyl-​2-​(1-​methylethyl)​-

HRID 59589Notes

Reaction equation

HRID 59589 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.[Pt]>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([CH:14]([CH3:16])[CH3:15])=[C:10]([CH:13]=1)[CH2:11][NH:4][CH:1]1[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 69828CyclopropylamineHCID 661614675-Chloro-2-(1-methylethyl)benzaldehyde

Product 1

HCID 66158544Benzenemethanamine, 5-​chloro-​N-​cyclopropyl-​2-​(1-​methylethyl)​-Yield 81.1%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Cyclopropylamine (3.26 g, 0.057 mol) was added to a solution of 5-chloro-2-isopropylbenzaldehyde (II) (10 g, 0.054 mol, 99.3 GC % by area) in methanol (100 ml) and the mixture was stirred at room temperature for 1 hour. Platinum on activated carbon (0.2 g, 5% Pt, dry) was subsequently added, the reaction vessel was flushed with nitrogen and pressurized to 6 bar with hydrogen at a maximum of 25° C. for 8 hours. The contents of the autoclave were filtered through Celite, washed with methanol and the solvent was distilled off under reduced pressure. N-(5-Chloro-2-isopropylbenzyl)cyclopropanamine (9.8 g, 96.8 GC-% by area, 78.0% of theory) was obtained as a light-yellow oil.

Workup

  1. customthe reaction vessel was flushed with nitrogen
  2. waitpressurized to 6 bar with hydrogen at a maximum of 25° C. for 8 hours
  3. filtrationThe contents of the autoclave were filtered through Celite
  4. washwashed with methanol
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cbb0d90022e34535a013f90677cf732f
Source dataset
uspto-grants-2016_09
Patent number
US09440908B2

Reaction notes

Loading…