Proton sponge → 6-Methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride
Reaction equation
[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]Participants
Procedure
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.).
Workup
- temperatureThe solution was cooled in an ice bath
- temperaturewas refluxed for 5 hours
- filtrationThe cooled mixture was filtered through a small column of silica gel
- washto wash the column
- customThe eluate was evaporated in vacuo
- dissolutionThe residual 1.35 g of thick oil was dissolved in 10 mL of methanol
- temperaturethe solution was refluxed for 24 hours
- customEvaporation of the methanol and crystallization of the residue from methanol
Sources & evidence
- ORD record
- ord-64faeccb38a24ccca6567b1d904c1e3e
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05112824
Reaction notes
Loading…