Diisopropylethylamine → 1-Benzyl-4-methylpiperidin-3-one

HRID 2122042노트

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HRID 2122042 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[CH:21]([OH:26])[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C>ClCCl.CS(C)=O>[CH2:12]([N:19]1[CH2:24][CH2:23][CH:22]([CH3:25])[C:21](=[O:26])[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

참가 물질

5

반응물 2

HCID 81531DiisopropylethylamineHCID 222535901-Benzyl-4-methylpiperidin-3-OL 4-methylbenzenesulfonate

생성물 1

HCID 120848281-Benzyl-4-methylpiperidin-3-one수율 72.97%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a solution of the product from Method D (9.8 grams/0.026 mol) and 31.7 mL of diisopropylethylamine dissolved in 250 mL of dichloromethane and cooled to 0° C. was added (dropwise) 12.4 grams of SO3 pyridine complex dissolved in 153 mL of dimethylsulfoxide over a 40 minute period. Once added, the reaction stirred for 1.5 hours at room temperature and was then quenched upon addition of 200 mL of saturated NaHCO3 (aq). The dichloromethane was removed in vacuo and the remaining aqueous residue extracted four times with diisopropyl ether (150 mL). The combined ether layers were washed four times with water (100 mL), dried over Na2SO4 and concentrated to dryness in vacuo affording 3.81 grams (72.97%) of the title compound as yellow oil. LRMS: 204 (M+1).

후처리

  1. additionwas added (dropwise) 12.4 grams of SO3 pyridine complex
  2. additionOnce added
  3. customwas then quenched upon addition of 200 mL of saturated NaHCO3 (aq)
  4. customThe dichloromethane was removed in vacuo
  5. extractionthe remaining aqueous residue extracted four times with diisopropyl ether (150 mL)
  6. washThe combined ether layers were washed four times with water (100 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-c6b46e52a69b422e9fe0e2136f9fc50f
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696567B2

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