Sodium Chloride → HCID 19036569, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][N:14]([CH2:16][CH2:17][NH:18][C:19](=[O:21])[CH3:20])[C:15]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[OH-:22].[K+].[Cl-].[Na+].[CH2:26]([OH:29])[CH2:27]O.[OH2:30]>>[C:19]([OH:21])(=[O:30])/[CH:20]=[CH:27]/[C:26]([OH:29])=[O:22].[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][C:11]3[CH:12]=[CH:13][N:14]([CH2:16][CH2:17][NH2:18])[C:15]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1Participants
Procedure
3.34 g of N-[2-(4,5-dihydro-6-methoxy-1H-benz[g]indol-1-yl)ethyl]-acetamide were heated to 140° for 23 hours. under argon in 5 ml of ethylene glycol/water 2:1 in the presence of 3.93 g of potassium hydroxide. The reaction mixture was left to cool and was poured into 300 ml of semi-concentrated sodium chloride solution. The mixture was extracted three times with diethyl ether, dried over sodium sulfate, filtered and evaporated. The crude product was dissolved in 30 ml of methanol and treated with 1.61 g of fumaric acid. The separated crystals were recrystallized from a total of 140 ml of methanol. 3.8 g (90%) of 2-(4,5-dihydro-6-methoxy-1H-benz[g]indol-1-yl)-ethylamine fumarate (1:1) were obtained as yellowish crystals with m.p. 198°.
Workup
- waitThe reaction mixture was left
- temperatureto cool
- extractionThe mixture was extracted three times with diethyl ether
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
- dissolutionThe crude product was dissolved in 30 ml of methanol
- additiontreated with 1.61 g of fumaric acid
- customThe separated crystals were recrystallized from a total of 140 ml of methanol
Sources & evidence
- ORD record
- ord-888407fef20745b4b71347d4a87b8ec1
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05646173
Reaction notes
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