4-(2,3-Epoxypropoxy)-2-ethoxycarbonyl-6-methyl indole → 4-(2-Hydroxy-3-isopropylamino-propoxy)-2-ethoxycarbonyl-6-methylindole
Reaction equation
[O:1]1[CH2:20][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2>C(N)(C)C>[OH:1][CH:2]([CH2:20][NH:9][CH:8]([CH3:15])[CH3:7])[CH2:3][O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2.0 g 4-(2,3-epoxypropoxy)-2-ethoxycarbonyl-6-methyl indole are dissolved in 25 ml isopropylamine. The solution is kept for two days at room temperature and then heated to boiling for 8 to 10 hours. Excessive isopropyl amine is removed in vacuum and the residue triturated with ether. The crude product is dissolved in small amounts of isopropanol during heating. After the addition of 0.42 ml glacial acetic acid, the solution is allowed to cool. The precipitated deposit is aspirated and recrystallized from small amounts of isopropanol. There is obtained 1.6 g (55% of theory) 4-(2-hydroxy-3-isopropylamino-propoxy)-2-ethoxycarbonyl-6-methylindole as acetate; m.p. 163°-165° C.
Workup
- temperatureheated
- waitto boiling for 8 to 10 hours
- customExcessive isopropyl amine is removed in vacuum
- customthe residue triturated with ether
- dissolutionThe crude product is dissolved in small amounts of isopropanol
- temperatureduring heating
- additionAfter the addition of 0.42 ml glacial acetic acid
- temperatureto cool
- customrecrystallized from small amounts of isopropanol
Sources & evidence
- ORD record
- ord-de57965652cd4d15bbd359605de12e6f
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04229464
Reaction notes
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