Benzyl Bromide → Ethyl-1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate

HRID 962730노트

반응식

HRID 962730 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:11]([N:19]1[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>O1CCCC1.Cl.C(OCC)(=O)C>[C:11]([N:19]1[CH2:24][CH2:23][C:22]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1)(=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 10545888Ethyl-1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매3회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

A stirred solution of 176 mL of commercial 1M lithium bistrimethylsilylamide in tetrahydrofuran was diluted with 100 mL of tetrahydrofuran and cooled to -78° C. under inert atmosphere. A solution of 44 g of ethyl 1-benzoyl-4-piperidinecarboxylate in 200 mL of tetrahydrofuran was added dropwise keeping the temperature below -60° C., followed by 21 mL of benzyl bromide. The resulting mixture was allowed to warm and stir overnight, diluted with 200 mL of 1N hydrochloric acid, 200 mL of ethyl acetate and separated. The organic layer was washed with 200 mL of 1N hydrochloric acid, dried over MgSO4, and concentrated. The residue was dissolved in 300 mL of toluene, filtered and concentrated under reduced pressure. Drying under reduced pressure gave 56.3 g of ethyl 1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate as a viscous oil homogeneous by thin layer chromatography, eluting with 1:1 ethyl acetate: hexane, 1H NMR (300 MHz, CDCl3) 1.20 (t, 3H), 1.40 (m, 1H), 1.60 (m, 1H), 2.07 (m, 1H), 2.22 (m, 1H), 2.85 (d, 2H), 3.08 (m, 1H), 3.65 (m, 1H), 4.12 (q, 2H), 4.65 (m, 1H), 7.04 (m, 2H), 7.24 (m, 3H), 7.38 (m, 5H).

후처리

  1. customthe temperature below -60° C.
  2. temperatureto warm
  3. customseparated
  4. washThe organic layer was washed with 200 mL of 1N hydrochloric acid
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in 300 mL of toluene
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customDrying under reduced pressure

출처 및 근거

ORD 기록
ord-6d23b3f6273848aa891bf1bb8d8c5a54
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760054

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