1-Heptanamine → Benzamide, 4-butyl-N-heptyl-

HRID 359995Notes

Reaction equation

HRID 359995 reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C(N(CC)CC)C.[CH2:16]([C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]>C(Cl)Cl.O>[CH2:1]([NH:8][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][C:20]([CH2:16][CH2:17][CH2:18][CH3:19])=[CH:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

6

Reactant 3

HCID 81271-HeptanamineHCID 8471TriethylamineHCID 1200494-Butylbenzoyl chloride

Product 1

HCID 13733121Benzamide, 4-butyl-N-heptyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a cold solution of 16 g of n-heptylamine and 29.0 ml of triethylamine in 300 ml of methylene chloride was added dropwise a solution of 27.4 g of 4-butylbenzoylchloride in 100 ml of methylene chloride. The resulting mixture was stirred at room temperature for 41/2 hours and diluted with water. The organic layer was washed with 1N sodium hydroxide, brine, dried, and evaporated. The residual solid was recrystallized from hexane to yield N-heptyl-4-n-butylbenzamide, mp 37°-38° C.

Workup

  1. washThe organic layer was washed with 1N sodium hydroxide, brine
  2. customdried
  3. customevaporated
  4. customThe residual solid was recrystallized from hexane

Sources & evidence

ORD record
ord-d852d53ff89640e4a4d801a4a89030ea
Source dataset
uspto-grants-1991_03
Patent number
US05003106

Reaction notes

Loading…