N-[(5-Chloro-2-isopropylphenyl)methylene]cyclopropanamine → Benzenemethanamine, 5-​chloro-​N-​cyclopropyl-​2-​(1-​methylethyl)​-

HRID 59590Notes

Reaction equation

HRID 59590 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([CH:8]=[N:9][CH:10]2[CH2:12][CH2:11]2)[CH:7]=1>[Pt].CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:13]([CH3:15])[CH3:14])=[C:6]([CH:7]=1)[CH2:8][NH:9][CH:10]1[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 89875637N-[(5-Chloro-2-isopropylphenyl)methylene]cyclopropanamine

Product 1

HCID 66158544Benzenemethanamine, 5-​chloro-​N-​cyclopropyl-​2-​(1-​methylethyl)​-Yield 94.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Platinum on activated carbon (5 g, 5% Pt, dry) was added to a solution of N-[(5-chloro-2-isopropylphenyl)methylene]cyclopropanamine (III) (160.8 g, 0.725 mol) in methanol (1350 ml). The reaction vessel was subsequently flushed with nitrogen and pressurized with 6 bar of 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 of the formula (I) (153.5 g, 97.1 GC-% by area, 91.9% of theory) was obtained as a light-yellow oil.

Workup

  1. customThe reaction vessel was subsequently flushed with nitrogen
  2. filtrationThe contents of the autoclave were filtered through Celite
  3. washwashed with methanol
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f0b7fa8a83fc42299a480f6248aca433
Source dataset
uspto-grants-2016_09
Patent number
US09440908B2

Reaction notes

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