Benzonitrile → 1-Phenyl-cyclopropylamine

HRID 533472

반응식

HRID 533472 반응식
[C:1](#[N:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][CH2:10][Mg+].[Br-].B(F)(F)F.CCOCC>CCOCC.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[C:2]1([C:1]2([NH2:8])[CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 7505BenzonitrileHCID 8000Boron trifluoride etherateHCID 178461630HCID 178461630, 화합물

생성물 1

HCID 1945491-Phenyl-cyclopropylamine수율 31.5%

시약·촉매·용매 2

HCID 178460666HCID 178460666, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

To benzonitrile (1.03 g, 10 mmol) in ether (50 ml) at −70° C. was added Ti(OiPr)4 (3.22 ml, 11 mmol) and EtMgBr (3M in ether, 7.34 mL, 22 mmol) dropwise, the resulting yellow suspension was warmed up to room temperature over 1 h. After stirring for additional 30 min, the dark brown solution was added BF3.Et2O (2.47 mL, 20 mL) at room temperature. The mixture was further stirred for 1 h, and was quenched by 1N HCl (30 mL) and 5N NaOH (30 mL), the suspension was extracted with ether, ether layer was combined, concentrated to give crude residue, which was purified by column (Hexanes/EtOAc, 2:1 to 1:9) to give 1-phenylcyclopropanamine (420 mg).

후처리

  1. stirringThe mixture was further stirred for 1 h
  2. customwas quenched by 1N HCl (30 mL) and 5N NaOH (30 mL)
  3. extractionthe suspension was extracted with ether, ether layer
  4. concentrationconcentrated
  5. customto give crude residue, which
  6. customwas purified by column (Hexanes/EtOAc, 2:1 to 1:9)

출처 및 근거

ORD 기록
ord-a95c49d72ce0490fafa98d752a9964c4
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853230B2

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