Carbon tetrabromide → 4-(3-(2-Bromoethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamine

HRID 1095599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1095599
[CH3:1][N:2]([CH3:27])[C:3]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19]O)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Br:28]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:28][CH2:19][CH2:18][C:17]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]=1[CH:6]1[CH2:7][CH2:8][C:3]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([N:2]([CH3:27])[CH3:1])[CH2:4][CH2:5]1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 236585632-(2-(4-(Dimethylamino)-4-phenylcyclohexyl)-1H-indol-3-yl)ethanol

Produkt 1

HCID 667836244-(3-(2-Bromoethyl)-1H-indol-2-yl)-N,N-dimethyl-1-phenylcyclohexanamineAusbeute 52,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-[2-(4-Dimethylamino-4-phenyl-cyclohexyl)-1H-indol-3-yl]-ethanol (Example 219, 3.20 g, 8.8 mmol) was dissolved in abs. CH2Cl2 (50 ml) at RT and tetrabromomethane (4.39 g, 13.2 mmol) was added. Triphenylphosphine (3.61 g, 12.6 mmol) was then added at RT. The solution was stirred at RT for 2.5 h and then concentrated i. vac. Flash chromatography of the residue with 300 g of silica gel and ethyl acetate/ethanol (1:2) gave 1.98 g of contaminated product, 1 N NaOH was added to this and the mixture was extracted three times with CHCl3. The organic phase was dried over Na2SO4 and concentrated i. vac. Yield: 1.57 g (42%)

Aufarbeitung

  1. concentrationconcentrated i

Quellen und Nachweise

ORD-Eintrag
ord-8e41f29428d64667acb1e46ae745fc4c
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138187B2

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