Triethylamine → 2-(2',5'-Dimethoxybenzoyl)-1-methylene-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1647318Notes

Reaction equation

HRID 1647318 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5](Cl)=[O:6].[CH3:14][C:15]1[C:24]2[C:19](=[C:20]([O:29][CH3:30])[C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=2)[CH2:18][CH2:17][N:16]=1.C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][C:4]=1[C:5]([N:16]1[CH2:17][CH2:18][C:19]2[C:24](=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[C:20]=2[O:29][CH3:30])[C:15]1=[CH2:14])=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 873642,5-Dimethoxybenzoyl chlorideHCID 157445311-Methyl-5,6,7-trimethoxy-3,4-dihydroisoquinoline

Product 1

HCID 157445322-(2',5'-Dimethoxybenzoyl)-1-methylene-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinolineYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A solution of compound 45 (746 mg, 3.7 mmol) in anhydrous benzene (2 mL) was slowly added at room temperature to a solution of compound 44 (880 mg, 3.7 mmol) in anhydrous benzene (10 mL) containing triethylamine (568 mg, 5.6 mmol, 0.78 mL). The resulting solution was heated at reflux with stirring under Ar for 2 h. White NH4Cl precipitated and was removed by filtration. The filtrate was evaporated to dryness and the residue was subjected to flash chromatography (ether:triethylamine, 99:1 by volume, silica gel 230-300 mesh) to give compound 46 as an oil (1.3 g, 87.8%): 1H NMR (CDCl3, 200 MHz) δ6.87 (s, 1H), 6.85 (d, 1H, J=10 Hz), 6.80 (d, 1H, J=3 Hz), 6.70 (d, 1H, J=10 Hz), 5.21 (s, br 1H), 4.55 (s, br, 1H), 3.90 (s, 6H), 3.88 (s, 3H), 3.84 (s, 3H), 3.75 (s, 3H), 3.41 (s, br, 2H), 2.88 (t, 2H, J=6 Hz). CIMS (isobutane) m/e 400 (MH+, 100).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux
  3. customWhite NH4Cl precipitated
  4. customwas removed by filtration
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-fa4823a31ad945249b1d55c50623e4e0
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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