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

HRID 14105

反応式

HRID 14105 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-b39dd9b74d0445a48965b470e709adbe
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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