Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylate → 1-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

HRID 1068491노트

반응식

HRID 1068491 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)([C:20](OCC)=[O:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(OCC)C>[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([CH2:20][OH:21])([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=2)[CH2:16][CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 21193210Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 211933021-Benzyl-4-hydroxymethyl-4-(3-methylphenylamino)piperidine

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

반응 조건

온도
0 °C

실험 절차

To a slurry of lithium aluminum hydride (330 mg, 8.7 mmol) in anhydrous diethyl ether (25 mL) at 0° C., a solution of ethyl 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylate (2.8 g, 7.94 mmol) in diethyl ether (10 mL) was added dropwise with the temp. of the reacting mixture maintained below 10° C. The resulting mixture was stirred at 0° C. for 30 min, and quenched with successive addition of water (0.33 mL), 15% aqueous NaOH (0.33 mL), and water (1 mL). The resultant slurry was stirred at room temp. for 30 min., and was filtered through a small plug of Celite. The filtrate was washed brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to provide the title alcohol as white solid.

후처리

  1. temperatureof the reacting mixture maintained below 10° C
  2. customquenched with successive addition of water (0.33 mL), 15% aqueous NaOH (0.33 mL), and water (1 mL)
  3. stirringThe resultant slurry was stirred at room temp. for 30 min.
  4. filtrationwas filtered through a small plug of Celite
  5. washThe filtrate was washed brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-47c93e2e1ef64b808d486ba30339d813
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06248756B1

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