4-Cyanobenzaldehyde → HCID 46869800, 화합물

HRID 882335노트

반응식

HRID 882335 반응식
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=1)#[N:13].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.O>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][CH2:18][C:17]2[CH:20]=[CH:21][C:14]([C:12]#[N:13])=[CH:15][CH:16]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 660424-CyanobenzaldehydeHCID 2723716Tranylcypromine hydrochlorideHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 46869800HCID 46869800, 화합물수율 19%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A mixture of (trans)-2-phenylcyclopropanamine hydrochloride (0.25 g, 1.50 mmol) and 4-cyanobenzaldehyde (0.22 g, 1.65 mmol) in CH2Cl2 (8 mL) and water (0.5 mL) was vigorously stirred at room temperature for 10 min. Then, NaBH(OAc)3 (0.41 g, 1.95 mmol) was slowly added and stirring continued for 1.5 h. The reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL), the organic layer was dried over anhydrous Na2SO4, filtered and, after removal of the solvent, the residual oil was purified by column chromatography on silica gel (1% MeOH/CH2Cl2) affording 0.07 g of 4-({[(trans)-2-phenylcyclopropyl]amino}methyl)benzonitrile [Rf=0.6 (5% MeOH/CH2Cl2), colorless oil, 19% yield].

후처리

  1. stirringstirring
  2. waitcontinued for 1.5 h
  3. washThe reaction mixture was washed with an aqueous saturated solution of NaHCO3 (10 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customafter removal of the solvent
  7. customthe residual oil was purified by column chromatography on silica gel (1% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-e811af39cc6b43f8a860b3b77b10df35
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993808B2

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