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

HRID 327398Notes

Reaction equation

HRID 327398 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-dc431fe2c63742daafd4a5bb569f15bc
Source dataset
uspto-grants-1993_12
Patent number
US05273974

Reaction notes

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