2-Methyl-4-heptanone → 2-Methylheptan-4-amine

HRID 1686100Notes

Reaction equation

HRID 1686100 reaction equation
[CH3:1][CH:2]([CH2:4][C:5](=O)[CH2:6][CH2:7][CH3:8])[CH3:3].C([O-])(=O)C.[NH4+].C([BH3-])#[N:16].[Na+]>CO>[CH3:1][CH:2]([CH2:4][CH:5]([NH2:16])[CH2:6][CH2:7][CH3:8])[CH3:3]

Participants

5

Reactant 3

HCID 693782-Methyl-4-heptanoneHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 144181752-Methylheptan-4-amineYield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-methylheptan-4-one (4.24 g, 33.07 mmol), in methanol (60 mL), were added ammonium acetate (25.50 g, 330.71 mmol) and sodium cyanoborohydride (2.08 g, 33.07 mmol). The reaction mixture was stirred at room temperature for about 24 hours. The solvent was removed under reduced pressure and the residue was diluted with water and basified with 15% NaOH aqueous and extracted with ether. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated to give 3.3 g of 2-methylheptan-4-amine (77%). MS (M+H, 130).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water and basified with 15% NaOH aqueous
  3. extractionextracted with ether
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c4fe0d92dbbf4c898e9987adf9c4afb9
Source dataset
uspto-grants-2012_04
Patent number
US08148536B2

Reaction notes

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