p-Anisoyl chloride → HCID 69475072, compound

HRID 853796Notes

Reaction equation

HRID 853796 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH2:20][NH:19][CH2:18][CH2:17]2.C(N(CC)CC)C>ClCCl>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH2:20][N:19]([C:7]([C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:8])[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 69475072HCID 69475072, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-benzoyl chloride (2.35 g) was added dropwise to a solution of 6-methoxy-1,2,3,4-tetrahydro-isoquinoline (0.75 g) and triethylamine (1.54 mL) in dichloromethane (40 mL) at 0° C. After 18 h at room temperature, the reaction was washed with 1N NaOH (2×50 mL), then water (2×50 mL). The organic extract was dried over sodium sulfate, filtered through celite and concentrated. The (6-methoxy-3,4-dihydro-1H-isoquinolin-2-yl)-(4-methoxy-phenyl)-methanone (0.95 g) product was obtained after purification by chromatography on silica gel (eluant: methylene chloride).

Workup

  1. washthe reaction was washed with 1N NaOH (2×50 mL)
  2. extractionThe organic extract
  3. dry with materialwas dried over sodium sulfate
  4. filtrationfiltered through celite
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4dbf578a6b1a43a18fb4baa389efef9a
Source dataset
uspto-grants-2007_08
Patent number
US07256201B2

Reaction notes

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