HCID 11011939, compound → HCID 18958303, compound

HRID 2379268Notes

Reaction equation

HRID 2379268 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2/[C:5]/1=[CH:14]\[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:3])[CH3:2]>C(Cl)Cl>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6]([CH2:7][CH2:8][CH2:9][CH:10]=2)=[C:5]1[CH2:14][C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 11011939HCID 11011939, compound

Product 1

HCID 18958303HCID 18958303, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.1 g of (E)-2-acetyl-1,2,S,4,5,6,7,8-octahydro-1-(p-methoxybenzylidene)isoquinoline (prepared according to Example 1) in 120 ml of methylene chloride was heated at reflux for 2 hours under argon. The solvent was then distilled off at 30° C./20 mbar. The residue, 2.3 g of a colorless oil, contained 61% of the desired product according to GC. Column chromatography and crystallization from isopropyl ether gave 700 mg of 2-acetyl-1 -(p-methoxybenzyl)-2,3,4,6,7,8-hexahydroisoquinoline, which was pure according to thin-layer chromatography and gas chromatography, as white crystals. M.p. 48°-50° C.

Workup

  1. temperatureat reflux for 2 hours under argon
  2. distillationThe solvent was then distilled off at 30° C./20 mbar
  3. customColumn chromatography and crystallization from isopropyl ether

Sources & evidence

ORD record
ord-6f7fe3c3fcf349268a8a3cb41d166935
Source dataset
uspto-grants-1994_11
Patent number
US05360908

Reaction notes

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