Octanoyl chloride → HCID 10270288, compound

HRID 1744739Notes

Reaction equation

HRID 1744739 reaction equation
[CH2:1]([NH:9][C:10]([C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.[C:25](Cl)(=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:1]([NH:9][C:10]([C@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:25](=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 8124Octanoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 58606954(2R)-N-Octyl-2-piperidinecarboxamide

Product 1

HCID 10270288HCID 10270288, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-(+)-2-piperidinecarboxylic acid n-octyl amide (23) (100 mg; 0.416 mmol) is dissolved in methylene chloride (3 mL) at ambient temperature. Triethylamine (63 mg; 0.624 mmol) is added and the solution cooled in an ice-bath. Octanoyl chloride (74 mg; 0.458 mmol) is added dropwise via syringe. The solution is stirred for 15 minutes and then allowed to warm to ambient temperature. After stirring for an additional 4.5 hours, the solution is poured onto saturated sodium bicarbonate solution and extracted with methylene chloride (20 mL). The methylene chloride extract is washed with water, dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography using a gradient elution (0%→40% ethyl acetate in hexanes) affording the desired product (28) as an oil. ISMS: MH+367.4

Workup

  1. temperaturethe solution cooled in an ice-bath
  2. stirringAfter stirring for an additional 4.5 hours
  3. extractionextracted with methylene chloride (20 mL)
  4. extractionThe methylene chloride extract
  5. washis washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is purified via silica gel chromatography
  10. washa gradient elution (0%→40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7823737fc2994dd29657553f66dafd19
Source dataset
uspto-grants-2006_03
Patent number
US07018642B2

Reaction notes

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