Benzylamine → HCID 19107606, compound

HRID 1646539Notes

Reaction equation

HRID 1646539 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][CH:10]([CH2:12][C:13](=O)[CH2:14][CH2:15][CH2:16][CH3:17])[CH3:11].C([BH3-])#N.[Na+].C(N(CC)CC)C>CO.CCCCCC.C(OC(=O)C)C>[CH2:1]([NH:8][CH:13]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:12][CH:10]([CH3:11])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 5225662-Methyl-4-octanoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19107606HCID 19107606, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylamine (3.1 ml, 28 mmol) was added to a stirred mixture of 2-methyloctan-4-one (4.0 g, 28 mmol) and 3 Å molecular sieves in dry methanol (40 ml) under argon. The mixture was stirred at room temperature overnight. Sodium cyanoborohydride (1.77 g, 28 mmol) was added and the mixture stirred overnight. Stirring was stopped and the solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride. The mixture was filtered, concentrated, ethyl acetate added and the mixtures washed with water. The organics were dried over anhydrous magnesium sulphate, filtered and concentrated to give a yellow oil. Chromatography (silica: 1% triethylamine and 10% ethylacetate in hexane) gave N-benzyl-2-methyl-4-aminooctane (3.0 g, 46%) as a yellow oil.

Workup

  1. stirringthe mixture stirred overnight
  2. stirringStirring
  3. customthe solution was decanted, from the molecular sieves, into saturated aqueous ammonium chloride
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated
  6. additionethyl acetate added
  7. washthe mixtures washed with water
  8. dry with materialThe organics were dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a yellow oil

Sources & evidence

ORD record
ord-6c1b6dc866604a97a6feb410b61d472c
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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