Aluminum(III) Chloride → 1'-Benzyl-6-chloro-3,4-dihydrospiro[chromene-2,4'-piperidine]

HRID 270046노트

반응식

HRID 270046 반응식
[Al+3].[Cl-].[Cl-].[Cl-].[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]2([CH2:26][C:25](=O)[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=3)[O:18]2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl>[CH2:5]([N:12]1[CH2:17][CH2:16][C:15]2([CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([Cl:28])[CH:23]=3)[O:18]2)[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 128879541'-Benzyl-6-chlorospiro[chroman-2,4'-piperidin]-4-one

생성물 1

HCID 598336421'-Benzyl-6-chloro-3,4-dihydrospiro[chromene-2,4'-piperidine]수율 65.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred suspension of AlCl3 (3.04 g, 22.8 mmol) in dichloromethane (75 ml) tert-butylamine-borane (1:1) (3.98 g, 45.8 mmol) was added at 0° C., and the stirring was continued for 15 min at this temperature to obtain a clear solution. A solution of 1′-benzyl-6-chlorospiro[chromene-2,4′-piperidin]-4(3H)-one (2.61 g, 7.6 mmol) in dichloromethane (15 ml) was added dropwise. The stirring was continued for 2 h at 0° C. and for 3 h at room temperature. The reaction mixture was quenched by dropwise addition of 0.1 N aq. HCl. After the gas evolution has ceased, the layers were separated. The organic layer was washed with 0.1 N HCl (2×50 ml) and brine (50 ml), and dried over Na2SO4. The solvent was removed in vacuo to afford subtitle compound as colourless solid (1.63 g, 65%).

후처리

  1. additionwas added at 0° C.
  2. customto obtain a clear solution
  3. waitThe stirring was continued for 2 h at 0° C. and for 3 h at room temperature
  4. customThe reaction mixture was quenched by dropwise addition of 0.1 N aq. HCl
  5. customthe layers were separated
  6. washThe organic layer was washed with 0.1 N HCl (2×50 ml) and brine (50 ml)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-b55a5ac9468c4b5695c09e32add1c227
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07449475B2

반응 노트

불러오는 중…