Methyl iodide → N,N-dibenzyl-N-{[1-(2-methoxy-2-methylpropyl)piperidin-4-yl]methyl}amine

HRID 1743819ノート

反応式

HRID 1743819 の反応式
[H-].[Na+].[CH2:3]([N:10]([CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([CH3:29])([OH:28])[CH3:27])[CH2:21][CH2:20]1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH3:31]>O1CCCC1.CN(C)C=O>[CH2:3]([N:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:18][CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]([O:28][CH3:31])([CH3:29])[CH3:27])[CH2:21][CH2:20]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 222364861-{4-[(Dibenzylamino)methyl]piperidin-1-yl}-2-methylpropan-2-ol

生成物 1

HCID 22236488N,N-dibenzyl-N-{[1-(2-methoxy-2-methylpropyl)piperidin-4-yl]methyl}amine収率 24.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of sodium hydride (abt. 60% in mineral oil, 342 mg, 8.6 mmol) in a mixture of tetrahydrofuran (20 mL) and N,N-dimethylformamide (10 mL) was added a solution of 1-{4-[(dibenzylamino)methyl]piperidin-1-yl}-2-methylpropan-2-ol (EXAMPLE 4, Step 4, 3.0 g, 8.2 mmol) in tetrahydrofuran (20 ml) at 0° C. Afer being stirred at the same temperature for 30 min, 0.53 mL (8.6 mmol) of iodomethane was added to the mixture. The mixture was stirred at ambient temperature for 3 days. The mixture was partitioned between ethyl acetate and water. After extraction with ethyl acetate, the combined organic phase was dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography on amine gel eluting with hexane/ethyl acetate (100:1) to afford 0.76 g (24%) of the title compound as colorless amorphous.

後処理

  1. stirringThe mixture was stirred at ambient temperature for 3 days
  2. customThe mixture was partitioned between ethyl acetate and water
  3. extractionAfter extraction with ethyl acetate
  4. dry with materialthe combined organic phase was dried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography on amine gel
  7. washeluting with hexane/ethyl acetate (100:1)

出典と根拠

ORDレコード
ord-d3908d20ec564dc0b88edab949441bdd
出典データセット
uspto-grants-2006_03
特許番号
US07012080B2

反応ノート

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