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

HRID 1086853ノート

反応式

HRID 1086853 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-a58487bb61324654adcfbdc1b011cb55
出典データセット
uspto-grants-1991_07
特許番号
US05032598

反応ノート

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