Methylamine → N-methyl-8-phenyloctanamide

HRID 1281465

반응식

HRID 1281465 반응식
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:23][NH2:24]>C(Cl)Cl.CCOCC>[CH3:23][NH:24][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 5202738-Phenyloctanoic acid

생성물 1

HCID 22237455N-methyl-8-phenyloctanamide수율 83%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of 8-phenyl octanoic acid (28.6 g, 129.8 mmol, 1 eq) in CH2Cl2 (100 mL) cooled to 0° C. was added oxalyl chloride (17 mL, 195 mmol, 1.5 eq) dropwise via an addition funnel over 30 minutes. Upon the completion of the addition, the ice bath was removed and the reaction was stirred at rt for 2 h. It was then heated at reflux for 30 minutes. The reaction was cooled to rt and concentrated in vacuo to afford a yellow oil. It was added as a solution in Et2O (100 mL) to a solution of condensed methyl amine (˜20 mL) in Et2O (200 mL) at −78° C. Immediately, a white precipitate formed. The cold bath was removed and the reaction was allowed to stir overnight warming to rt under a stream of N2. The residue was washed with Et2O and concentrated to afford N-methyl-8-phenyloctanamide (25.2 g, 83%) as a yellow-white solid. 1H NMR.(CDCl3) δ 7.68-7.10 (m, 5H); 5.42 (bs, 1H); 3.80 (m, 3H); 2.60 (m, 2H); 2.18 (m, 2H); 1.60 (m, 4H); 1.30 (m, 8H).

후처리

  1. additionUpon the completion of the addition
  2. customthe ice bath was removed
  3. temperatureIt was then heated
  4. temperatureat reflux for 30 minutes
  5. temperatureThe reaction was cooled to rt
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow oil
  8. customImmediately, a white precipitate formed
  9. customThe cold bath was removed
  10. stirringto stir overnight
  11. temperaturewarming to rt under a stream of N2
  12. washThe residue was washed with Et2O
  13. concentrationconcentrated

출처 및 근거

ORD 기록
ord-18fb9e34ce9a49d29f3b94c1ec5b60fd
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451827B2

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