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Dichloromethane → 4-[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-2-hydroxypropoxy]benzonitrile

HRID 1743703
ノート
印刷プレビュー

反応式

HRID 1743703 の反応式
[CH2:1]([N:8]1[CH2:14][CH:13]2[NH:15][CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:16]1[CH2:18][CH:17]1[CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1.C(Cl)Cl>CC(O)C.O>[CH2:1]([N:8]1[CH2:14][CH:13]2[N:15]([CH2:18][CH:17]([OH:16])[CH2:19][O:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH:10]([CH2:11][CH2:12]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 27643014-(2-Oxiranylmethoxy)benzenecarbonitrileHCID 124305943-Benzyl-3,8-diazabicyclo[3.2.1]octane

生成物 1

HCID 222354394-[3-(3-Benzyl-3,8-diazabicyclo[3.2.1]oct-8-yl)-2-hydroxypropoxy]benzonitrile収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 3776
Isopropanol
溶媒

反応条件

温度
60 °C

実験手順

A mixture of 3-benzyl-3,8-diazabicyclo[3.2.1]octane (3.46 g, 17.1 mmol; from Preparation B, step (e) above) and 4-(2-oxiranylmethoxy)benzonitrile (3.00 g, 17.1 mmol; prepared as described in international patent application WO 99/31100) in 2-propanol (70 mL) and H2O (7 mL) was stirred at 60° C. for 22 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in CH2Cl2 (200 mL) and washed with water (50 mL) and brine (50 mL). The organic layer was dried (NaSO4), filtered and concentrated in vacuo to give the crude product. Flash chromatography on silica gel eluting with CH2Cl2:CMA (8:1) gave 5.74 g (89%) of the sub-title compound as a yellow oil.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (200 mL)
  3. washwashed with water (50 mL) and brine (50 mL)
  4. dry with materialThe organic layer was dried (NaSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product

出典と根拠

ORDレコード
ord-22d5a7ff5b8b457da924a510e450c6b0
出典データセット
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07012074B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート