1-Benzyl-4-methyl-4-phenylpiperidine → 4-Methyl-4-phenylpiperidine

HRID 382711노트

반응식

HRID 382711 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:20][C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

참가 물질

5

반응물 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidine

생성물 2

HCID 30195114-Methyl-4-phenylpiperidineHCID 108016621-Benzyl-4-methyl-4-phenylpiperidine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 284Formic Acid용매

실험 절차

Freshly prepared methanolic formic acid solution (4.4% by weight, 70 mL) was added to 1-benzyl-4-methyl-4-phenylpiperidine (3.23 g, 12.2 mmol, 1.00 equiv). To the resulting solution was added palladium on carbon (10% Pd, 2.00 g). The mixture was stirred at room temperature for 24 hours. The solid was filtered out and washed with MeOH (30 mL), H2O (15 mL), CH2Cl2 (30 mL) and MeOH (15 mL). The combined filtrate and washings were concentrated, and the residue was dissolved in CH2Cl2 (50 mL) and H2O (10 mL). The aqueous phase was adjusted to pH 11 by addition of 1 N aqueous NaOH. The organic phase was separated, dried over MgSO4 and concentrated. The residual oil was purified by flash chromatography (SiO2, CHCl3—MeOH—NH3 (2.0 M in MeOH) 100:4:0 to 100:20:10) to afford 1.20 g of 1-benzyl-4-methyl-4-phenylpiperidine and 1.10 g (51%, 82% based on unrecovered starting material) of 4-methyl-4-phenylpiperidine, which was characterized spectroscopically.

후처리

  1. filtrationThe solid was filtered out
  2. washwashed with MeOH (30 mL), H2O (15 mL), CH2Cl2 (30 mL) and MeOH (15 mL)
  3. concentrationThe combined filtrate and washings were concentrated
  4. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
  5. additionThe aqueous phase was adjusted to pH 11 by addition of 1 N aqueous NaOH
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residual oil was purified by flash chromatography (SiO2, CHCl3—MeOH—NH3 (2.0 M in MeOH) 100:4:0 to 100:20:10)

출처 및 근거

ORD 기록
ord-b5683ee545034f509e1b238760a61f19
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06310076B1

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