2,3-Dimethylbenzaldehyde → N-(2,3-Dimethylbenzyl)cyclopropanamine

HRID 561775

Reaction equation

HRID 561775 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH:11]1([NH2:14])[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+].[BH4-].[Na+]>CO>[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:14][CH:11]1[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 342242,3-DimethylbenzaldehydeHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 43090146N-(2,3-Dimethylbenzyl)cyclopropanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2,3-dimethylbenzaldehyde (1 eq.), cyclopropylamine (1.2 eq.) and sodium bicarbonate (1.5 eq.) were heated at reflux in MeOH (0.5 M) for 1 h. The reaction mixture was then cooled in ice and sodium borohydride (1.2 eq.) was introduced portionwise. Following the completion of addition, the reaction mixture was warmed to RT and stirred at RT for 1 h. The volatiles were then removed in vacuo and the resulting residue was partitioned between H2O and CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a light yellow oil.

Workup

  1. temperaturewere heated
  2. temperatureThe reaction mixture was then cooled in ice
  3. additionthe completion of addition
  4. customThe volatiles were then removed in vacuo
  5. customthe resulting residue was partitioned between H2O and CH2Cl2
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered

Sources & evidence

ORD record
ord-be14b1427d9e452483eb7bab427ff737
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Linked notes

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