Triethylamine → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-chlorosulfonylpiperidin-4-ylmethyl)amine

HRID 429839ノート

反応式

HRID 429839 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:30][S:31](O)(=[O:33])=[O:32].P(Cl)(Cl)(Cl)(Cl)Cl>ClCCl.C1C=CC=CC=1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:31]([Cl:30])(=[O:33])=[O:32])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 15546287(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

生成物 1

HCID 53697435(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-chlorosulfonylpiperidin-4-ylmethyl)amine収率 70%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine (0.2 grams, 0.66 mmole) and triethylamine (0.15 grams, 1.48 mmole) in dichloromethane (4 ml) at 0° C. was added dropwise a solution of chlorosulfonic acid (0.08 grams, 0.66 mmol) in dichloromethane (0.5 ml). The mixture was stirred at room temperature for 16 hours, and the solvent was removed under reduced pressure. To the residue was added benzene (4 ml) and phosphorous pentachloride (0.14 grams, 0.67 mmole). The mixture was heated under reflux for 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and 1N sodium hydroxide. The organic layer was washed with brine, dried over sodium sulfate and concentrated to give (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-chlorosulfonylpiperidin-4-ylmethyl)amine as a viscous oil (0.18 grams, 70%), M+H 401.

後処理

  1. customthe solvent was removed under reduced pressure
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was partitioned between ethyl acetate and 1N sodium hydroxide
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-dd0cecd1dbb84b35b6abbe9207d2f810
出典データセット
uspto-grants-2001_11
特許番号
US06319920B1

反応ノート

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