Acetyl chloride → 1-(5-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethanone

HRID 1059717Notes

Reaction equation

HRID 1059717 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][NH:7][CH2:8]2.C(N(CC)CC)C.[C:20](Cl)(=[O:22])[CH3:21]>C(Cl)Cl>[C:20]([N:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[CH:12][C:3]=2[O:2][CH3:1])[CH2:8]1)(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 139482495-Methoxy-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 152349571-(5-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)ethanoneYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of step (b) (6.26 g, 31.4 mmol) and triethylamine (9.6 ml, 69.0 mmol) in CH2Cl2 (150 ml) was added acetyl chloride (2.7 ml, 37.7 mmol) at 0° C. over a period of 15 min. The reaction mixture was stirred at room temperature for 18 h after which time the solution was washed sequentially with H2O and saturated aqueous sodium bicarbonate solution, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified on silica gel eluting with EtOAc to afford the subtitle compound as an orange oil (6.07 g, 94%). Rf 0.65 (CH2Cl2/MeOH/0.88NH3 90/10/1, v/v). MS m/z 206 (MH+).

Workup

  1. washwas washed sequentially with H2O and saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. customevaporated under reduced pressure
  4. customThe crude product was purified on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-f4fa12a91a404a8a947cb11b6ce7c757
Source dataset
uspto-grants-2003_02
Patent number
US06521629B2

Reaction notes

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