Ethanol → 2-Methyl-1-[7-(benzyloxy)indol-3-yl]prop-2-ylamine

HRID 1272209

Reaktionsgleichung

Reaktionsgleichung von HRID 1272209
[CH3:1][C:2]([N+:22]([O-])=O)([CH3:21])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(O)C>[Ni].O1CCCC1>[CH3:21][C:2]([NH2:22])([CH3:1])[CH2:3][C:4]1[C:12]2[C:7](=[C:8]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 702EthanolHCID 220147783-(2-Methyl-2-nitropropyl)-7-(benzyloxy)indole

Produkt 1

HCID 220147792-Methyl-1-[7-(benzyloxy)indol-3-yl]prop-2-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A mixture of 3-(2-methyl-2-nitropropyl)-7-(benzyloxy)indole (25.0 g, 77.1 mmol), Raney Nickel® (9.5 g wet lump), and 3A ethanol (250 mL) is pressurized to 50 psig with H2 and is heated to 60° C. After 1 hour, the mixture is cooled to ambient temperature. The mixture is diluted with tetrahydrofuran (100 mL) and is warmed to 50° C. The catalyst is removed by filtration and the cake is rinsed with 50° C. tetrahydrofuran (4×50 mL). The filtrate is concentrated to a solid which is dried in a 50° C. vacuum oven to provide 22.41 (99%) of 2-methyl-1-[7-(benzyloxy)indol-3-yl]prop-2-ylamine. MS (ES+) m/z 295 (100%).

Aufarbeitung

  1. temperaturethe mixture is cooled to ambient temperature
  2. temperatureis warmed to 50° C
  3. customThe catalyst is removed by filtration
  4. washthe cake is rinsed with 50° C. tetrahydrofuran (4×50 mL)
  5. concentrationThe filtrate is concentrated to a solid which
  6. customis dried in a 50° C. vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-66fe8ead5ffa4e0aba745f09a26647ef
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208505B2

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