Methanesulfonyl chloride → HCID 18361514, compound

HRID 382988Notes

Reaction equation

HRID 382988 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.[CH3:30][S:31]([Cl:34])(=[O:33])=[O:32]>N1C=CC=CC=1.O>[ClH:34].[C:1]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:2]=[CH:3][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][N:16]3[S:31]([CH3:30])(=[O:33])=[O:32])=[CH:11][CH:10]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 18361536HCID 18361536, compound

Product 1

HCID 18361514HCID 18361514, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 7-(4-biphenylyl)methoxy-3-[2-(N,N-dimethylamino)ethyl]-1,2,3,4-tetrahydroquinoline (110 mg) in pyridine (5 ml) was added methanesulfonyl chloride (0.03 ml) in an ice bath. The reaction mixture was stirred at room temperature for 3 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. 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=1:2) and converted into its hydrochloride, which was then recrystallized from ethanol-ethyl acetate to obtain the titled compound (88 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:2)
  6. customwas then recrystallized from ethanol-ethyl acetate

Sources & evidence

ORD record
ord-9240c08f608a45649c4f99737110a0ef
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Reaction notes

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