Allylamine → Ammonium Hydroxide

HRID 1442868Notes

Reaction equation

HRID 1442868 reaction equation
[CH:1]1([CH:4]=[O:5])[CH2:3][CH2:2]1.[CH2:6]([NH2:9])[CH:7]=[CH2:8].C([BH3-])#N.[Na+]>CO>[NH4+:9].[OH-:5].[CH:1]1([CH2:4][NH:9][CH2:6][CH:7]=[CH2:8])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 7853AllylamineHCID 123114CyclopropanecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 2

HCID 14923Ammonium HydroxideHCID 20460830N-2-Propen-1-ylcyclopropanemethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Cyclopropanecarboxaldehyde (1.00 g, 14.3 mmol) was added dropwise to a stirred solution of allylamine (4.07 g, 71.3 mmol) in MeOH (100 mL) and stirring was continued at ambient temperature for 2 h, then sodium cyanoborohydride (0.94 g, 15.0 mmol) was added. After 3 h, the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH:NH4OH—100:0:0 to 90:10:1 to provide the title compound. MS: m/z=112 (M+1).

Workup

  1. waitAfter 3 h
  2. customthe solvent was removed under reduced pressure
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-f528493d596f4c1cbc1bc533a0b1f6b5
Source dataset
uspto-grants-2010_02
Patent number
US07659300B2

Reaction notes

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