Sodium hydride → 7-[(2-Piperidinoethoxy)methyl]-2-phenylbenzofuran hydrochloride

HRID 1639026Notes

Reaction equation

HRID 1639026 reaction equation
[OH:1][CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[H-].[Na+].Cl.[Cl:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>CS(C)=O.O>[ClH:21].[N:24]1([CH2:23][CH2:22][O:1][CH2:2][C:3]2[C:11]3[O:10][C:9]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)=[CH:8][C:7]=3[CH:6]=[CH:5][CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 145149497-Hydroxymethyl-2-phenylbenzofuran

Product 1

HCID 198403137-[(2-Piperidinoethoxy)methyl]-2-phenylbenzofuran hydrochlorideYield 51%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

7-Hydroxymethyl-2-phenylbenzofuran (1.57 g) is dissolved in dimethylsulfoxide (10 ml), and sodium hydride (60% oil dispersion) (0.57 g) is added thereto. After the mixture is stirred for 10 minutes, N-(2-chloroethyl)piperidine hydrochloride (1.35 g) is added to the mixture and the mixture is stirred at room temperature for 4 hours. The mixture is diluted with water and extracted with ethyl acetate. The extract is washed with water, dried and concentrated under reduced pressure to remove solvent. The residue is converted to its hydrochloride and recrystallized from ethyl acetate, whereby 7-[(2-piperidinoethoxy)methyl]-2-phenylbenzofuran hydrochloride (1.32 g) is obtained. Yield: 51%.

Workup

  1. stirringthe mixture is stirred at room temperature for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customto remove solvent
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c84902389f744f2fad958c64feb3dde5
Source dataset
uspto-grants-1989_11
Patent number
US04882340

Reaction notes

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