Triethylamine → 4-Heptyl-N-hydroxy-N-methylbenzamide

HRID 365050Notes

Reaction equation

HRID 365050 reaction equation
Cl.[CH3:2][NH:3][OH:4].C(N(CC)CC)C.[CH2:12]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1COCC1.O.CCOC(C)=O>[CH2:12]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([N:3]([OH:4])[CH3:2])=[O:24])=[CH:21][CH:20]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 77906N-methylhydroxylamine hydrochlorideHCID 1708644-Heptylbenzoyl chloride

Product 1

HCID 202388064-Heptyl-N-hydroxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of N-methylhydroxylamine hydrochloride (701 mg, 2 eq.) in 20 ml of THF:H2O (1:1) with triethylamine (1.75 ml, 3.0 eq.) was added 4-n-heptyl benzoic acid chloride (1.0 g, 4.2 mmol). The solution was stirred for 1/2 hour at 0° C. then allowed to warm to room temperature and stir overnight. The reaction mixture was diluted with EtOAc and the organic layer washed with H2O, 1N HCl (2×), and brine, then dried over anhydrous MgSO4. Concentration in vacuo gave an oil which was flash chromatographed on LPS-1 silica gel eluting with (1:1) hexane:EtOAc. Product containing fractions were concentrated in vacuo to yield title product, 448 mg (43%) as a light yellow oil which solidified upon standing. TLC (1:1) Hexane:EtOAc Rf =0.18, UV+PMA. Product streaks to baseline.

Workup

  1. temperatureto warm to room temperature
  2. stirringstir overnight
  3. washthe organic layer washed with H2O, 1N HCl (2×), and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentration in vacuo
  6. customgave an oil which
  7. customchromatographed on LPS-1 silica gel eluting with (1:1) hexane
  8. additionProduct containing fractions
  9. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-70e2912fc069405c83e747dff2cf2c9e
Source dataset
uspto-grants-1986_08
Patent number
US04607053

Reaction notes

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