Diethyl Ether → 1,4-Dibenzyl-4-cyanopiperidine

HRID 1839

反応式

HRID 1839 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].[CH:9]([N-]C(C)C)([CH3:11])[CH3:10].[Li+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCOCC.[CH2:30]1[CH2:34]O[CH2:32][CH2:31]1>C1CCCCC1>[CH2:17]([N:6]1[CH2:7][CH2:8][C:3]([CH2:32][C:31]2[CH:11]=[CH:9][CH:10]=[CH:34][CH:30]=2)([C:1]#[N:2])[CH2:4][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 5

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 1382234-CyanopiperidineHCID 2724682Lithium diisopropylamide

生成物 1

HCID 227417421,4-Dibenzyl-4-cyanopiperidine

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
-50 °C

実験手順

A solution of 15 g of 4-cyanopiperidine in 250 ml of THF is cooled to -50° C., 190 ml of a 1.5M solution of lithium diisopropylamide in cyclohexane are added dropwise and the mixture is stirred for 30 minutes at -50° C. 34 ml of benzyl bromide are then added and the mixture is stirred for 3 hours after the temperature has been allowed to rise to RT. The reaction mixture is poured into an ice/concentrated HCl mixture, ether is added and the precipitate formed is filtered off and washed with water. The precipitate is taken up with water, rendered alkaline to pH 12 by the addition of concentrated NaOH solution, and extracted with ether, the organic phase is dried over MgSO4 and the solvent is evaporated off to give 31.7 g of the expected product after crystallization from pentane. M.p.=92° C.

後処理

  1. stirringthe mixture is stirred for 3 hours after the temperature
  2. customto rise to RT
  3. additionis added
  4. customthe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water
  7. additionby the addition of concentrated NaOH solution
  8. extractionextracted with ether
  9. dry with materialthe organic phase is dried over MgSO4
  10. customthe solvent is evaporated off

出典と根拠

ORDレコード
ord-2ea15a5f5b1a44b1851d5776c77eecc6
出典データセット
uspto-grants-1998_03
特許番号
US05726313

関連ノート

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