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

HRID 596874

반응식

HRID 596874 반응식
[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]

참가 물질

10

반응물 6

HCID 313Hydrochloric Acid3회HCID 126652-Piperidone2회HCID 14798Sodium HydroxideHCID 209351-HydroxypiperidineHCID 167261392-[(4-Methoxyphenyl)methyl]-1,3,3-trimethylpiperidin-4-oneHCID 178506846HCID 178506846, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ae190895684a4db69ca756c37cf010e0
출처 데이터셋
uspto-grants-1977_03
특허 번호
US04012392

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