Heptanoic Acid → N-(Cyclohexylmethyl)heptanamide

HRID 1725207Notes

Reaction equation

HRID 1725207 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[C:9](O)(=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:3]1([CH2:2][NH:1][C:9](=[O:16])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 8094Heptanoic AcidHCID 76688CyclohexanemethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 68856580N-(Cyclohexylmethyl)heptanamideYield 92%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of aminomethylcyclohexane (0.34 g, 3.0 mmol) in methylene chloride (30 mL) was added heptanoic acid (0.39 g, 3 mmol) and DMAP(0.37 g, 3.0 mmol) followed by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.57 g, 3.0 mmol) and the reaction mixture was stirred at room temperature overnight. The mixture was diluted with methylene chloride (100 mL), and the organic phase was washed with 5% HCl (3×75 mL), aqueous NaHCO3 (75 mL) and brine (75 mL), and dried over Na2SO4. Concentration in vacuo afforded 0.62 g (92%) of an oil, which then crystallised.

Workup

  1. washthe organic phase was washed with 5% HCl (3×75 mL), aqueous NaHCO3 (75 mL) and brine (75 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-2a21cda1a57a41fea1536ecf4bdbe372
Source dataset
uspto-grants-2009_02
Patent number
US07488844B2

Reaction notes

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