Hydrochloric Acid → 4-(4-Methoxybenzyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline

HRID 1579257ノート

反応式

HRID 1579257 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]=1.Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2O[CH:24]2C(OCC)=O)=[CH:19][CH:18]=1.C(O)C>O.CO.CCCCCC.C1C=CC=CC=1>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]2[C:5]3[CH2:6][CH2:7][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:4]=3[CH2:3][CH2:2][NH:1]2)=[CH:19][CH:18]=1

参加物

9

反応物 4

HCID 313Hydrochloric Acid2 回HCID 702EthanolHCID 860252-Oxiranecarboxylic acid, 3-(4-methoxyphenyl)-, ethyl esterHCID 190478584-(2-Aminoethyl)-1,2-dihydronaphthalene

生成物 1

HCID 541999694-(4-Methoxybenzyl)-1,2,3,4,5,6-hexahydrobenz[f]isoquinoline収率 56%

試薬・触媒・溶媒 4

HCID 241Benzene溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 8058Hexane溶媒

実験手順

A mixture 28.4 g. (0.138 mole) of the hydrochloride salt of 2-aminoethyl)-1,2-dihydronaphthalene (II) in water (800 ml.) was acidified to pH 3 by the addition of hydrochloric acid. The resulting mixture was heated under reflux under a nitrogen atmosphere and with vigorous stirring, a solution of 38.0 g. (0.172 mole) of ethyl 3-(4-methoxyphenyl)-2,3-epoxypropionate in 200 ml. of ethanol was added dropwise over a period of 8 hours. Reflux was continued for 16 hours, then 300 ml. of concentrated hydrochloric acid was added. After a further 4 hours under reflux, the mixture was allowed to cool, and benzene (800 ml.), hexane (200 ml.) and methanol (200 ml.) were added, the mixture was shaken and the aqueous layer separated. The aqueous layer was basic and extracted with methylene chloride to give a 56 percent yield of product (III). The nuclear magnetic resonance spectrum of the product was consistent with the structure.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux under a nitrogen atmosphere and with vigorous stirring
  3. temperatureReflux
  4. temperatureAfter a further 4 hours under reflux
  5. temperatureto cool
  6. customthe aqueous layer separated
  7. extractionextracted with methylene chloride

出典と根拠

ORDレコード
ord-a948aae4b79d45a599f04bfb20df8dfb
出典データセット
uspto-grants-1976_01
特許番号
US03931188

反応ノート

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