Proton sponge → 6-Methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride

HRID 1586715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586715
[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH:11]([CH:16]3[CH2:21][CH2:20][N:19](C)[CH2:18][CH2:17]3)[C:12]2=[O:15])=[CH:8][CH:7]=1)(=[O:4])=[O:3].CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.[Cl:39]C(OC(Cl)=O)C>ClCCCl>[ClH:39].[CH3:1][S:2]([NH:5][C:6]1[CH:14]=[C:13]2[C:9]([CH2:10][CH:11]([CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:12]2=[O:15])=[CH:8][CH:7]=1)(=[O:3])=[O:4]

Komponenten

5

Edukt 3

HCID 88675Proton spongeHCID 5213051-Chloroethyl chloroformateHCID 149859946-Methanesulfonamido-2-(1-methyl-4-piperidyl)indan-1-one

Produkt 1

HCID 197591836-Methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.35 g (0.00419 mol) of 6-methanesulfonamido-2-(1-methyl-4-piperidyl)indan-1-one in 46 mL of 1,2-dichloroethane was added 1.35 g (0.0063 mol) of 1,8-bis(dimethylamino)naphthalene. The solution was cooled in an ice bath and 1.80 g (0.0126 mol) of 1-chloroethylchloroformate was added dropwise over 5 minutes. The mixture was allowed to warm to room temperature and then was refluxed for 5 hours. The cooled mixture was filtered through a small column of silica gel using methylene chloride to wash the column. The eluate was evaporated in vacuo. The residual 1.35 g of thick oil was dissolved in 10 mL of methanol, and the solution was refluxed for 24 hours. Evaporation of the methanol and crystallization of the residue from methanol afforded 6-methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride as a hemi methanol solvate salt: mp 254°-256° (dec.).

Aufarbeitung

  1. temperatureThe solution was cooled in an ice bath
  2. temperaturewas refluxed for 5 hours
  3. filtrationThe cooled mixture was filtered through a small column of silica gel
  4. washto wash the column
  5. customThe eluate was evaporated in vacuo
  6. dissolutionThe residual 1.35 g of thick oil was dissolved in 10 mL of methanol
  7. temperaturethe solution was refluxed for 24 hours
  8. customEvaporation of the methanol and crystallization of the residue from methanol

Quellen und Nachweise

ORD-Eintrag
ord-462c44f4396446cca36bfb16ef3909e6
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05215989

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