Methane → Alosetron Hydrochloride

HRID 2379154Notes

Reaction equation

HRID 2379154 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]1=2.[ClH:23].C>C(O)C>[ClH:23].[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:22])[N:12]([CH2:15][C:16]3[N:17]=[CH:18][NH:19][C:20]=3[CH3:21])[CH2:13][CH2:14][C:3]1=2

Participants

5

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 2099Alosetron

Product 1

HCID 60758Alosetron Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,3,4,5-Tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (1.00 g) was suspended in ethanol (40 ml) and concentrated hydrochloric acid (1.00 ml) was added. The mixture was warmed to 40° and charcoal (0.25 g) was added. The resulting suspension was stirred and warmed for 5 min. and then filtered. The filtrate was evaporated in vacuo to ca. 20 ml and was allowed to cool to 20°. Ether (40 ml) was added with stirring over 5 min., and the mixture was stored at 4° overnight. The resulting precipitate was filtered off, washed with ether (2×10 ml), dried in vacuo at room temperature for 2 h and then at 70° for 7 h to give the title compound (0.95 g), m.p. 288°-291°.

Workup

  1. temperatureThe mixture was warmed to 40°
  2. temperaturewarmed for 5 min.
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo to ca. 20 ml
  5. temperatureto cool to 20°
  6. additionEther (40 ml) was added
  7. stirringwith stirring over 5 min.
  8. filtrationThe resulting precipitate was filtered off
  9. washwashed with ether (2×10 ml)
  10. customdried in vacuo at room temperature for 2 h

Sources & evidence

ORD record
ord-e8e9075b27484d55875725552eb5b616
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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