1-Heptanamine → Pentanamide, N-heptyl-5-hydroxy-

HRID 249096

Reaction equation

HRID 249096 reaction equation
[C:1]1(=[O:7])[O:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:8]([NH2:15])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]>C1(C)C=CC=CC=1>[CH2:8]([NH:15][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][OH:6])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 81271-HeptanamineHCID 10953Delta-Valerolactone

Product 1

HCID 10262728Pentanamide, N-heptyl-5-hydroxy-Yield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Delta valerolactone (40 g, 0.4 mole) was added dropwise with stirring to n-heptylamine (50.6 g, 0.4 mole) so that the temperature of the mixture was maintained at 85° to 90° C. Heat was applied and the temperature raised to 110° C. over 20 minutes after which the temperature was maintained at 110° to 115° C. for a further 6 hours (after 3 hours N.M.R. indicated that the reaction was 90 to 95% complete). Toluene (200 ml, 173 g) was added and the solution cooled to 0° C. with stirring. After 1 hour at 0° C., the solid was collected and washed successively with ice cold toluene (50 ml, 43 g) and n-heptane (50 ml, 34 g). The material was dried at room temperature overnight to give the product. (81.6 g (95% yield) m.p. 53° to 54° C.).

Workup

  1. temperaturewas maintained at 85° to 90° C
  2. temperatureHeat
  3. temperaturewas maintained at 110° to 115° C. for a further 6 hours (after 3 hours N.M.R
  4. temperaturethe solution cooled to 0° C.
  5. customthe solid was collected
  6. washwashed successively with ice cold toluene (50 ml, 43 g) and n-heptane (50 ml, 34 g)
  7. customThe material was dried at room temperature overnight
  8. customto give the product

Sources & evidence

ORD record
ord-a2db769c74e14bb0bf039bde9917aa5b
Source dataset
uspto-grants-1993_05
Patent number
US05212318

Linked notes

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