Dihydrobenzofuran → 5-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-2,3-dihydrobenzofuran

HRID 327398노트

반응식

HRID 327398 반응식
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12](Cl)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[CH2:17][CH2:16]1.[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:22]2[CH:21]=[CH:20][C:19]3[O:15][CH2:16][CH2:17][C:18]=3[CH:23]=2)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 10329DihydrobenzofuranHCID 6451240Aluminum(III) ChlorideHCID 104659513-(1-Acetyl-4-piperidinyl)propionyl chloride

생성물 1

HCID 191084645-[3-(1-Acetylpiperidin-4-yl)-1-oxopropyl]-2,3-dihydrobenzofuran수율 78%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To 200 ml of 1,2-dichloroethane were added 9.65 g (44 mmol) of 3-(1-acetylpiperidin-4-yl)propionic acid chloride and 10.65 g (89 mmol), of 2,3-dihydrobenzofuran. To the mixture was added 12.82 g (96 mmol) of aluminum chloride in limited amounts, then the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into ice-water, which was subjected to extraction with methylene chloride. Organic layers were combined and washed with water and dried over anhydrous sodium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography (ethyl acetate) to give 10.47 g (78%) of 5-[3-(1-acetylpiperidin-4-yl)-1-oxopropyl]-2,3-dihydrobenzofuran. Recrystallization from methylene chloride--diethyl ether gave colorless needles, m.p. 93°-95° C.

후처리

  1. extractionwas subjected to extraction with methylene chloride
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationby distilling off the solvent
  5. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-dc431fe2c63742daafd4a5bb569f15bc
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273974

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