Benzylamine → 12-Methoxy-N-(phenylmethyl)dodecanamide

HRID 618307Notes

Reaction equation

HRID 618307 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:32]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 1961175912-Methoxydodecanoyl chloride

Product 1

HCID 979711912-Methoxy-N-(phenylmethyl)dodecanamideYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylamine (486 mg, 4.5 mmol) in 20 mL of methylene chloride at 0° C. was added dropwise diisopropylethylamine (0.45 ml, 5 mmol) followed by the title product of example 11 (1.0 g, 4 mmol). After stirring at room temperature for 6 days, the reaction mixture was washed successively with 1N HCl, water, saturated NaHCO3, water and brine, dried over magnesium sulfate, filtered and concentrated. The residue was dissolved in anhydrous methanol and passed through a basic ion exchange resin and eluted with anhydrous methanol. Concentration afforded the title compound (895 mg) as a white solid, m.p. 77.7-79.4° C. (DSC). The structure was supported by NMR, infrared spectroscopy, elemental analysis, and mass spectroscopy.

Workup

  1. washthe reaction mixture was washed successively with 1N HCl, water, saturated NaHCO3, water and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in anhydrous methanol
  6. washeluted with anhydrous methanol
  7. concentrationConcentration

Sources & evidence

ORD record
ord-4b2c67a2c815495faa482d4f0aed6950
Source dataset
uspto-grants-1999_09
Patent number
US05952377

Reaction notes

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