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

HRID 541217노트

반응식

HRID 541217 반응식
[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

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate2회

생성물 1

HCID 682889074-(Azepan-4-yl)benzonitrile수율 99.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-d21c4ea4cfb4407e8225741c5872002f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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