2-Methylimidazole → Ondansetron

HRID 2309425Notes

Reaction equation

HRID 2309425 reaction equation
Cl[CH2:2][CH:3]1[C:15](=[O:16])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:17])[C:6]=2[CH2:5][CH2:4]1.[CH3:18][C:19]1[NH:20][CH:21]=[CH:22][N:23]=1>CN(C=O)C>[CH3:17][N:7]1[C:6]2[CH2:5][CH2:4][CH:3]([CH2:2][N:20]3[CH:21]=[CH:22][N:23]=[C:19]3[CH3:18])[C:15](=[O:16])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2

Participants

4

Reactant 2

HCID 127492-MethylimidazoleHCID 135197113-(Chloromethyl)-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one

Product 1

HCID 4595OndansetronYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(chloromethyl)-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (0.50 g) and 2-methyl-1H-imidazole (1.60 g) in dry DMF was stirred under nitrogen at 90° for 3.75 h, and then poured onto water (25 ml). The suspension was stirred for 1 h, and the solid filtered off, washed with water (3×20 ml) and dried in vacuo at 50°. Column chromatography of this solid (0.53 g) eluting with a mixture of dichloromethane, ethanol and 0.88 aqueous ammonia (150:10:1) afforded the title compound (0.45 g) m.p. 228°-229°. This material was identical to the product from Example 7 by t.l.c. and n.m.r.

Workup

  1. additionpoured onto water (25 ml)
  2. filtrationthe solid filtered off
  3. washwashed with water (3×20 ml)
  4. customdried in vacuo at 50°
  5. washColumn chromatography of this solid (0.53 g) eluting with a mixture of dichloromethane, ethanol and 0.88 aqueous ammonia (150:10:1)

Sources & evidence

ORD record
ord-479f48777623463ca7b577b96d76eef7
Source dataset
uspto-grants-1987_09
Patent number
US04695578

Reaction notes

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