Triethylamine → 1-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl ester

HRID 48569Notes

Reaction equation

HRID 48569 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:24]([O:25][CH3:26])=[CH:23][C:7]([CH2:8][CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH3:22])=[C:16]([O:19][CH3:20])[CH:17]=3)[CH2:12][CH2:11]N2)=[CH:6][CH:5]=1.[CH2:27](N(CC)CC)C.[CH3:34][O:35][C:36](=[O:45])[CH:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CCOC(C)=O.CCCCCC>C1(C)C=CC=CC=1.C(Cl)Cl>[CH3:34][O:35][C:36](=[O:45])[CH2:37][C:38]1([CH:27]2[CH2:11][CH2:12][C:13]3[C:18](=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[CH:9]2[CH2:8][C:7]2[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[C:24]([O:25][CH3:26])[CH:23]=2)[CH:43]=[CH:42][CH:41]=[CH:40][CH2:39]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterHCID 16667431Isoquinoline, 1-((3,4-dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-, hydrochloride (1:1)HCID 21226206Ethyl acetate hexane

Product 1

HCID 697601251-[(3,4-Dimethoxy-benzyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-phenyl-acetic acid methyl esterYield 91.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a white suspension of 1-(4,5-dimethoxybenzyl)6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-hydrochloride (5 g, 0.013 mol) in dry toluene (50 ml), were added triethylamine (5.5 ml, 0.039 mol) and bromo-phenyl-acetic acid methyl ester (2.07 ml, 0.013 mol). The reaction mixture was stirred at reflux under argon for 20 h. After cooling, the mixture was diluted in CH2Cl2 and washed with water. The aqueous phase was extracted twice with CH2Cl2, the combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude brown-orange oil. Flash chromatography (AcOEt/hexane 1/1) gave 5.85 g (90%) of the title product as a brown-orange oil.

Workup

  1. temperatureat reflux under argon for 20 h
  2. temperatureAfter cooling
  3. washwashed with water
  4. extractionThe aqueous phase was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude brown-orange oil

Sources & evidence

ORD record
ord-ea68a220f4284ba196011734ad7e3a3e
Source dataset
uspto-grants-2004_03
Patent number
US06703392B2

Reaction notes

Loading…