Potassium Iodide → alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanol

HRID 866653노트

반응식

HRID 866653 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Cl[CH2:19][CH:20]([C:22]1[O:27][C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[O:24][CH:23]=1)[OH:21].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[O:27]1[C:26]2[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=2[O:24][CH2:23][CH:22]1[CH:20]([OH:21])[CH2:19][N:15]1[CH2:16][CH2:17][CH:12]([C:6]2[C:5]3[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=3)[NH:8][CH:7]=2)[CH2:13][CH2:14]1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 432245-Methoxy-3-(piperidin-4-yl)-1H-indoleHCID 12733300alpha-(Chloromethyl)-1,4-benzodioxin-2-methanol

생성물 1

HCID 20320076alpha-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanol수율 111.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4.6 g of 4-(5-methoxy-[1H]-indol-3-yl)-piperidine, 4.3 g of α-(chloromethyl)-1,4-benzodioxin-2-methanol, 4.4 g of sodium carbonate, 3.3 g of potassium iodide and 25 ml of dimethylformamide was heated with stirring at 100° C for 24 hours under a nitrogen atmosphere and then the mixture was cooled and filtered. The filter was washed with dimethylformamide and the filtrate was evaported under reduced pressure to dryness. The residue was taken up in a 1--1 mixture of water and methylene chloride and the organic phase was recovered by decantation, was washed, dried and evaporated to dryness under reduced pressure to obtain 9.1 g of α-(2,3-dihydro-1,4-benzodioxin-2-yl)-4-(5-methoxyl-[1H]-indol-3-yl)-1-piperidine-ethanol in the form of a mixture of 2 diastereoisomeric racemates in the form of a brown oil which was used as is for the next step.

후처리

  1. temperaturewas heated
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. washThe filter was washed with dimethylformamide
  5. additionThe residue was taken up in a 1--1 mixture of water and methylene chloride
  6. customthe organic phase was recovered by decantation
  7. washwas washed
  8. customdried
  9. customevaporated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-b77795fa04224a02b7fb77b39efcdcc0
출처 데이터셋
uspto-grants-1978_07
특허 번호
US04100291

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