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

HRID 382711ノート

反応式

HRID 382711 の反応式
[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

参加物

5

反応物 1

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

生成物 2

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 284Formic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b5683ee545034f509e1b238760a61f19
出典データセット
uspto-grants-2001_10
特許番号
US06310076B1

反応ノート

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