Gamma-Valerolactone → Pentanamide, N-heptyl-5-hydroxy-

HRID 374059

Reaction equation

HRID 374059 reaction equation
[C:1]1(=[O:7])O[CH:4]([CH3:5])[CH2:3][CH2:2]1.[CH2:8]([NH2:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CCCCCC.C(OCC)(=[O:24])C>C1(C)C=CC=CC=1>[CH2:8]([NH:15][C:5](=[O:24])[CH2:4][CH2:3][CH2:2][CH2:1][OH:7])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

6

Reactant 4

HCID 7921Gamma-ValerolactoneHCID 8058HexaneHCID 81271-HeptanamineHCID 8857Ethyl Acetate

Product 1

HCID 10262728Pentanamide, N-heptyl-5-hydroxy-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Part A. A solution of γ-valerolactone (25.0 g, 0.249 mol) in toluene (50 mL) and n-heptylamine (35.96 g, 0.312 mol) was heated to reflux for 18 hours under a nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, diluted with ethyl acetate (300 mL), washed with 1N aqueous HCl (50 mL), water, brine, dried over magnesium sulfate and concentrated to give a white solid. The product was crystallized from ethyl ether:hexane to give N-heptyl-5-hydroxypentanamide (41.8 g, 0.194 mol) as white plates, mp 55°-6°. 1H NMR (CDCl3) δ6.06(bs,1H), 3.61(t,2H), 3.24(q,2H), 3.19(bs,1H), 2.19(t,2H), 1.80-1.23(m,14H), 0.866(t,3H).

Workup

  1. temperatureto reflux for 18 hours under a nitrogen atmosphere
  2. washwashed with 1N aqueous HCl (50 mL), water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a white solid
  6. customThe product was crystallized from ethyl ether

Sources & evidence

ORD record
ord-b194f9f6266d49a58f6a356572f3a8c1
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Linked notes

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