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

HRID 14105

Reaktionsgleichung

Reaktionsgleichung von HRID 14105
[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-b39dd9b74d0445a48965b470e709adbe
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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