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

HRID 429839노트

반응식

HRID 429839 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 241Benzene용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dd0cecd1dbb84b35b6abbe9207d2f810
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319920B1

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