Triethylamine → Benzyl 4-acetylpiperidine-1-carboxylate

HRID 2105521노트

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HRID 2105521 반응식
Cl.[C:2]([CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:4])[CH3:3].CCN(CC)CC.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl.O>[C:2]([CH:5]1[CH2:10][CH2:9][N:8]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:7][CH2:6]1)(=[O:4])[CH3:3]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 441518974-Acetylpiperidinium chloride

생성물 1

HCID 19065050Benzyl 4-acetylpiperidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

4-Acetylpiperidine hydrochloride (4B-1, 5.0 g, 30.55 mmole) was taken up in CH2Cl2 (150 mL). To this was added Et3N (9.8 mL, 70.27 mmole) and the suspension became a solution. The mixture was cooled to 0° C. to which was added benzyl chloroformate (5.2 mL, 36.66 mmole). After the addition was complete the mixture was warmed to RT. After 18 hr the mixture was diluted with H2O. The layers were separated and the aqueous extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to afford benzyl 4-acetylpiperidine-1-carboxylate as an off-white solid (4B-2): 1H-NMR (500 MHz, CDCl3) δ 7.35 (m, 5H), 5.13 (s, 2H), 4.18 (bs, 2H), 2.88 (bs, 2H), 2.49 (m, 1H), 2.17 (s, 3H), 1.86 (bs, 2H), 1.55 (m, 2H).

후처리

  1. additionAfter the addition
  2. temperaturewas warmed to RT
  3. customThe layers were separated
  4. extractionthe aqueous extracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-321701c532a447f5987470bc7e8f4451
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579355B2

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