Octanoyl chloride → HCID 3425108, compound

HRID 882346Notes

Reaction equation

HRID 882346 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+].[C:20](Cl)(=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[Cl-].[NH4+]>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([NH:13][C:20](=[O:28])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 8124Octanoyl chlorideHCID 11430Potassium CarbonateHCID 13583DodecylamineHCID 25517Ammonium Chloride

Product 1

HCID 3425108HCID 3425108, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Into a 500 mL two-neck flask, dodecylamine (18.69 g) and DMAP (N,N-dimethyl-4-aminopyridine) (3.67) were added and nitrogen substitution was carried out. Subsequently, dichloromethane (150 mL) and potassium carbonate (16.67 g) were added to this. In a state in which this flask was cooled in an ice bath, a solution obtained by mixing dichloromethane (150 mL) and octanoic acid chloride (17.94 g) was dropwise added. After the dropwise addition was finished, the temperature was raised to room temperature, and the reaction was carried out for 4 hours. The end of the reaction was confirmed by gas chromatography, and 50 mL of saturated aqueous solution of ammonium chloride was added. After the resultant was stirred for 10 minutes, extraction was carried out with dichloromethane (100 mL), and the obtained organic phase was washed with 1M aqueous solution of hydrochloric acid (50 mL), saturated aqueous solution of sodium hydrogencarbonate (50 mL), and saturated aqueous solution of sodium chloride (50 mL). Removal of the solvent by reduced-pressure distillation was carried out using an evaporator, and recrystallization was carried out with dichloromethane-hexane. The yield of the object N-dodecyloctanoic acid amide was 89% (20.13 g, 89.42 mmol) in terms of dodecylamine.

Workup

  1. temperatureIn a state in which this flask was cooled in an ice bath
  2. customa solution obtained
  3. additionwas dropwise added
  4. additionAfter the dropwise addition
  5. additionwas added
  6. extractionextraction
  7. washthe obtained organic phase was washed with 1M aqueous solution of hydrochloric acid (50 mL), saturated aqueous solution of sodium hydrogencarbonate (50 mL), and saturated aqueous solution of sodium chloride (50 mL)
  8. customRemoval of the solvent
  9. distillationby reduced-pressure distillation
  10. customan evaporator, and recrystallization

Sources & evidence

ORD record
ord-e9cc75621811472b81d144d1de6f159c
Source dataset
uspto-grants-2015_03
Patent number
US08993814B2

Reaction notes

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