Butyl bromide → 2-Butyl-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

HRID 348897

Reaktionsgleichung

Reaktionsgleichung von HRID 348897
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[CH2:4][CH2:3][NH:2]1.C(N(CC)CC)C.Br[CH2:21][CH2:22][CH2:23][CH3:24]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:21]([N:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=2)[CH2:1]1)[CH2:22][CH2:23][CH3:24]

Komponenten

6

Edukt 3

HCID 8002Butyl bromideHCID 8471TriethylamineHCID 101762437-Cyano-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 210854272-Butyl-1,2,3,4-tetrahydroisoquinoline-7-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To an ice-cold, stirred solution of 1,2,3,4-tetrahydroisoquinoline-7-carbonitrile (J. Med. Chem. 1997, 40, 3997) (485 mg, 3.1 mmol) and triethylamine (0.47 mL, 3.4 mmol) in methylene chloride (5 mL) is added DMAP (37 mg, 0.3 mmol) and bromobutane (0.5 mL, 4.6 mmol). The reaction mixture is stirred for 20 h, diluted with methylene chloride, washed with water, and brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. ESI MS m/z 215 [M+H]+.

Aufarbeitung

  1. washwashed with water, and brine
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e1024372a3284b9ba6e67e06bda5c7e7
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176242B2

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