Hydrochloric Acid → 4-Ethyl-2-(p-methoxybenzyl)-1,3,3-trimethyl-4-piperidinol hydrochloride

HRID 596874

反応式

HRID 596874 の反応式
[ClH:1].[CH3:2][O:3][C:4]1[CH:20]=[CH:19][C:7]([CH2:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C:13](=[O:17])[CH2:12][CH2:11][N:10]2[CH3:18])=[CH:6][CH:5]=1.[OH-].[Na+].N1(O)CCC[CH2:25][CH2:24]1.N1CCCCC1=O.C([Li])C>CCOCC.CC(C)=O.O>[ClH:1].[CH2:24]([C:13]1([OH:17])[CH2:12][CH2:11][N:10]([CH3:18])[CH:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:20][CH:19]=2)[C:14]1([CH3:16])[CH3:15])[CH3:25]

参加物

10

反応物 6

HCID 313Hydrochloric Acid3 回HCID 126652-Piperidone2 回HCID 14798Sodium HydroxideHCID 209351-HydroxypiperidineHCID 167261392-[(4-Methoxyphenyl)methyl]-1,3,3-trimethylpiperidin-4-oneHCID 178506846HCID 178506846、化合物

生成物 1

HCID 214486164-Ethyl-2-(p-methoxybenzyl)-1,3,3-trimethyl-4-piperidinol hydrochloride収率 45%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

The hydrochloride (18 g) of 2-(p-methoxybenzyl)-1,3,3-trimethyl-4-piperidone is converted to the free base by shaking with ether and aqueous sodium hydroxide, followed by evaporation of the ethereal solution. The oily base is dissolved in 30 ml of absolute ether and subsequently reacted with ethyl lithium (3.6 g in 300 ml of benzene) under conditions as described in example 39. According to gaschromatographic examination, conversion to the piperidinol occurs to the extent of only 25 percent. After the addition of water the reaction mixture is worked up as described in example 39 and the crude mixture of piperidone and piperidonal so obtained is treated again with ethyl lithium (2.7 g in 250 ml of benzene). This procedure is repeated once more whereafter still 20 percent of the piperidone appears to be present. Processing as usually furnishes 19 g of an oily base, which is converted to the hydrochloride with the aid of ethanolic hydrogen chloride. After the addition of acetone and ether, 9 g of the above crystalline product separates. Yield 45%. Melting point 232 -234° C with decomposition.

後処理

  1. customfollowed by evaporation of the ethereal solution
  2. dissolutionThe oily base is dissolved in 30 ml of absolute ether
  3. customsubsequently reacted with ethyl lithium (3.6 g in 300 ml of benzene) under conditions
  4. custompiperidonal so obtained

出典と根拠

ORDレコード
ord-ae190895684a4db69ca756c37cf010e0
出典データセット
uspto-grants-1977_03
特許番号
US04012392

関連ノート

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