2-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]acetamide hydrochloride → 2-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamide

HRID 908973Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 908973
Cl.[CH3:2][N:3]([CH3:32])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:8][C:7](=[CH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:12])[CH2:6][CH2:5]1>[Pd].CO>[CH3:32][N:3]([CH3:2])[C:4]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9][CH2:8][CH:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=2)=[O:12])[CH2:6][CH2:5]1

Komponenten

4

Edukt 1

HCID 116553562-(4-Dimethylamino-4-phenylcyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]acetamide hydrochloride2×

Produkt 1

HCID 115833142-(4-Dimethylamino-4-phenylcyclohexyl)-N-[3-(1H-indol-3-yl)propyl]-acetamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

Palladium-on-charcoal (5%, 20 mg) was added to a solution of 2-(4-dimethylamino-4-phenyl-cyclohexylidene)-N-[3-(1H-indol-3-yl)propyl]-acetamide (base of Example 16; 305 mg, 0.734 mmol) in abs. methanol (30 ml). The reaction mixture was hydrogenated at RT under a pressure of 3 bar for 6 h. The catalyst was separated off over Celite and the filtrate was concentrated. After separation of the residue (289 mg) by chromatography on silica gel (20 g) with EA/methanol (2:1), the product was isolated as a beige-coloured oil in a yield of 29% (95 mg).

Aufarbeitung

  1. customThe catalyst was separated off over Celite
  2. concentrationthe filtrate was concentrated
  3. customAfter separation of the residue (289 mg) by chromatography on silica gel (20 g) with EA/methanol (2:1)
  4. customthe product was isolated as a beige-coloured oil in a yield of 29% (95 mg)

Quellen und Nachweise

ORD-Eintrag
ord-e670d0387b01441fa8879124f44e8433
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017630B2

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