Hydrazine hydrate (1:1) → (R)-2-[3-(2-aminopropyl)-1H-indol-7-yloxy]-N,N-diethyl-acetamide
Reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]([CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:17][C@H:18]([N:20]1C(=O)C2=CC=CC=C2C1=O)[CH3:19])=[O:5])[CH3:2].O.NN>C(O)C>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]([CH2:6][O:7][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[C:13]2[CH2:17][C@H:18]([NH2:20])[CH3:19])=[O:5])[CH3:32]Participants
Conditions
- Temperature
- 85 °C
Procedure
(R)-7-Diethylaminocarbonylmethyloxy-3-(2-phthalimidopropyl)indole 10.27 g was suspended in 100 ml of ethanol, and 2.5 ml of hydrazine monohydrate was added thereto. The suspension was heated to reflux in an oil bath of 85° C. For 3 hours. After cooling down, the resulting deposited insoluble materials were filtered off, and the filtrate was concentrated under reduced pressure. Ethyl acetate and a sodium hydroxide aqueous solution were added to the residue and distributed in liquid-liquid, and the organic layer was further washed with a sodium hydroxide aqueous solution and dried. The solution was evaporated under reduced pressure. The resulting residue was slowly crystallized, and dried under reduced pressure, whereby 6.90 g of the title compound was obtained in the form of a pale brownish white substance.
Workup
- temperatureThe suspension was heated
- temperatureAfter cooling down
- filtrationwere filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- additionEthyl acetate and a sodium hydroxide aqueous solution were added to the residue
- washthe organic layer was further washed with a sodium hydroxide aqueous solution
- customdried
- customThe solution was evaporated under reduced pressure
- customThe resulting residue was slowly crystallized
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-aa7188ec5e114b029020b4845f5c56a1
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115412B2
Reaction notes
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