Dichloromethane → 4-(Azepan-4-yl)benzonitrile

HRID 541217ノート

反応式

HRID 541217 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].C(Cl)Cl.FC(F)(F)C(O)=O>C(OCC)(=O)C>[NH:12]1[CH2:13][CH2:14][CH2:15][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate2 回

生成物 1

HCID 682889074-(Azepan-4-yl)benzonitrile収率 99.1%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a vial containing tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate (compound 40.3, 77 mg, 0.257 mmol, 1.0 equiv) was added DCM (500 μL) and trifluoroacetic acid (198 μL, 2.57 mmol, 10 equiv) and the mixture was stirred vented for 90 min. The mixture was diluted into ethyl acetate (5 mL) and washed with saturated sodium bicarbonate (5 mL). The aqueous was adjusted to pH 10-11 and extracted with addition ethyl acetate until no product remained. The combined organics were dried (Na2SO4), filtered and concentrated to obtain the title compound as a yellow oil (51 mg, theoretical). m/z (ES+) 201 (M+H)+.

後処理

  1. washwashed with saturated sodium bicarbonate (5 mL)
  2. extractionextracted with addition ethyl acetate until no product
  3. dry with materialThe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-d21c4ea4cfb4407e8225741c5872002f
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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