Methane → HCID 15616303, compound

HRID 2379155Notes

Reaction equation

HRID 2379155 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.[S:23](=[O:27])(=[O:26])([OH:25])[OH:24].C>C(O)C>[S:23]([OH:27])([OH:26])(=[O:25])=[O:24].[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 1118Sulfuric AcidHCID 2099Alosetron

Product 1

HCID 15616303HCID 15616303, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2,3,4,5-Tetrahydro-5-methyl-2-[(5-methyl-1H-imidazol-4-yl)methyl]-1H-pyrido[4,3-b]indol-1-one (0.81 g) was suspended in absolute ethanol (6 ml) and was warmed at 50° with concentrated sulphuric acid (0.15 ml). More ethanol (4 ml) was added and the mixture was stirred with charcoal (0.1 g). The suspension was then filtered and the collected solid was washed with ethanol (ca. 3 ml). The resulting filtrate was stirred for ca. 1 h at room temperature, tert-butyl methyl ether (10 ml) was added slowly and the mixture was stirred for 20 min. The precipitate was filtered off, washed with ethanol:tert-butyl methyl ether (1:1;6 ml), then with tert-butyl methyl ether (6 ml), and dried in vacuo at 40° for 4 days to give the title compound (0.4 g), m.p. 205°-209°.

Workup

  1. filtrationThe suspension was then filtered
  2. washthe collected solid was washed with ethanol (ca. 3 ml)
  3. additiontert-butyl methyl ether (10 ml) was added slowly
  4. stirringthe mixture was stirred for 20 min
  5. filtrationThe precipitate was filtered off
  6. washwashed with ethanol:tert-butyl methyl ether (1:1;6 ml)
  7. dry with materialwith tert-butyl methyl ether (6 ml), and dried in vacuo at 40° for 4 days

Sources & evidence

ORD record
ord-407b48770a334f4d9669784797f50f27
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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