1,2-Dichloroethane → (1,3-Dihydroisobenzofuran-1-yl)-(piperidin-4-yl)methanone hydrochloride

HRID 914919Notes

Reaction equation

HRID 914919 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([CH:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][O:17]2)=[O:15])[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:25]CCCl>ClC(OC(Cl)C)=O>[ClH:25].[CH:16]1([C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:18][O:17]1

Participants

4

Reactant 2

HCID 111,2-DichloroethaneHCID 22248144(1-Benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone

Product 1

HCID 22248211(1,3-Dihydroisobenzofuran-1-yl)-(piperidin-4-yl)methanone hydrochloride

Reagents, catalysts & solvents 1

HCID 5213051-Chloroethyl chloroformateSolvent

Procedure

After dissolving 517 mg of (1-benzylpiperidin-4-yl)-(1,3-dihydroisobenzofuran-1-yl)methanone in 5 ml of 1,2-dichloroethane, 0.49 ml of 1-chloroethyl chloroformate was added and the mixture was heated to reflux for 1 hour. The reaction solution was distilled off under reduced pressure, 5 ml of methanol was added to the residue and heating to reflux was continued for 1 hour. The reaction solution was distilled off under reduced pressure, saturated aqueous sodium bicarbonate solution was added and extraction was performed with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure to obtain 104 mg of (1,3-dihydroisobenzofuran-1-yl)-(piperidin-4-yl)methanone hydrochloride.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureto reflux for 1 hour
  4. distillationThe reaction solution was distilled off under reduced pressure, 5 ml of methanol
  5. additionwas added to the residue
  6. temperatureheating
  7. temperatureto reflux
  8. distillationThe reaction solution was distilled off under reduced pressure, saturated aqueous sodium bicarbonate solution
  9. additionwas added
  10. extractionextraction
  11. dry with materialThe extract was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-3dcc01c440c9405586c0283bcfa08853
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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