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

HRID 1579257Notes

Reaction equation

HRID 1579257 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a948aae4b79d45a599f04bfb20df8dfb
Source dataset
uspto-grants-1976_01
Patent number
US03931188

Reaction notes

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