Benzylamine → HCID 19107606, compound

HRID 1197655Notes

Reaction equation

HRID 1197655 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>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

7

Reactant 4

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

Product 1

HCID 19107606HCID 19107606, compoundYield 46%

Reagents, catalysts & solvents 2

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

Sources & evidence

ORD record
ord-005515668ff54d43bd1777313c1bb4ab
Source dataset
uspto-grants-1994_01
Patent number
US05276153

Reaction notes

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