Acetyl chloride → HCID 22998556, compound

HRID 1166551Notes

Reaction equation

HRID 1166551 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:15][NH:16]3)=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:37](Cl)(=[O:39])[CH3:38]>C1COCC1.O>[C:37]([N:16]1[C:17]2[C:12](=[CH:11][CH:10]=[C:9]([O:8][CH2:7][C:4]3[CH:3]=[CH:2][C:1]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:6][CH:5]=3)[CH:18]=2)[CH2:13][CH:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH2:15]1)(=[O:39])[CH3:38]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18361536HCID 18361536, compound

Product 1

HCID 22998556HCID 22998556, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(4-biphenylyl)methoxy-3-[2-(N,N-dimethylamino) ethyl]-1,2,3,4-tetrahydroquinoline (250 mg) in THF (17 ml) was added triethylamine (0.33 ml) followed by addition of acetyl chloride (0.09 ml) at 0° C. After stirring in an ice bath for one hr, the reaction mixture was further stirred at room temperature for one hr. The reaction mixture was diluted with water and extracted with ethyl acetate. oil The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent:ethyl acetate: hexane=1:20 to 1:6) and the resulting precipitated crystals were washed with diisopropyl ether to obtain the titled compound (210 mg).

Workup

  1. stirringthe reaction mixture was further stirred at room temperature for one hr
  2. extractionextracted with ethyl acetate
  3. washoil The organic layer was washed with saturated aqueous sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent:ethyl acetate: hexane=1:20 to 1:6)
  7. customthe resulting precipitated crystals
  8. washwere washed with diisopropyl ether

Sources & evidence

ORD record
ord-1dffd1c82bf74a8f83f195b0aba3cd35
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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