Dimethyl Sulfate → Ondansetron

HRID 2309420Notes

Reaction equation

HRID 2309420 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][CH:8]2[C:20](=[O:21])[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[NH:12][C:11]=3[CH2:10][CH2:9]2)[CH:4]=[CH:5][N:6]=1.[H-].[Na+].[CH3:24]OS(OC)(=O)=O>CN(C)C=O>[CH3:24][N:12]1[C:11]2[CH2:10][CH2:9][CH:8]([CH2:7][N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])[C:20](=[O:21])[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 108912241,2,3,9-Tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one

Product 1

HCID 4595Ondansetron

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 1,2,3,9-tetrahydro-3-[(2-methyl-1H-imidazol-1-yl)methyl]-4H-carbazol-4-one (1.0 g) in dry dimethylformamide (10 ml) was added dropwise under nitrogen to a stirred, ice-cooled suspension of sodium hydride (80% in oil; 0.11 g) in dry dimethylformamide (5 ml). After 0.5 h dimethylsulphate (0.34 ml) was added, and the solution stirred at room temperature for 4 h. The resultant solid was filtered off, washed with ice-cold dry dimethylformamide (2×5 ml) and dry ether (3×15 ml) and dried to give the title compound as a solid (0.25 g) m.p. 223°-224° (dec).

Workup

  1. temperaturecooled
  2. filtrationThe resultant solid was filtered off
  3. washwashed with ice-cold dry dimethylformamide (2×5 ml) and dry ether (3×15 ml)
  4. customdried

Sources & evidence

ORD record
ord-f3df745390184006ba0b719ee7ca9a0c
Source dataset
uspto-grants-1987_09
Patent number
US04695578

Reaction notes

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