Cyclopropanemethanamine → HCID 15341894, compound

HRID 1079104Notes

Reaction equation

HRID 1079104 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)=[CH:4][CH:3]=1.[CH:18]1([CH2:21][NH2:22])[CH2:20][CH2:19]1.[BH4-].[Na+]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH2:11][NH:22][CH2:21][CH:18]2[CH2:20][CH2:19]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 75646CyclopropanemethanamineHCID 6933013-[(4-chlorobenzyl)oxy]benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 15341894HCID 15341894, compoundYield 106.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

A solution of 62 g of 3-(4-chlorobenzyloxy)-benzaldehyde and 20 g of cyclopropylmethylamine in 750 ml of methanol was stirred at room temperature for 15 minutes. Thereto was slowly added 12 g of sodium borohydride with ice-cooling. The resulting mixture was stirred at the same temperature for 1 hour. The reaction mixture was dissolved in 1 liter of chloroform. The solution was washed with water, dried with anhydrous magnesium sulfate, and subjected to vacuum distillation to remove the solvent, whereby 81 g of 3-(4-chlorobenzyloxy)-N-cyclopropylmethylbenzylamine was obtained.

Workup

  1. temperaturecooling
  2. washThe solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationsubjected to vacuum distillation
  5. customto remove the solvent

Sources & evidence

ORD record
ord-a61fc6d10ff14ec3a87df595372b3830
Source dataset
uspto-grants-1996_08
Patent number
US05550292

Reaction notes

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