Morpholine → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(morpholine-4-sulfonyl)-piperidin-4-ylmethyl]amine

HRID 429840노트

반응식

HRID 429840 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][N:20]([S:23](Cl)(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(N(C(C)C)CC)(C)C>O1CCCC1>[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:23]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 53697435(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-chlorosulfonylpiperidin-4-ylmethyl)amine

생성물 1

HCID 69168638(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(morpholine-4-sulfonyl)-piperidin-4-ylmethyl]amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(1-chlorosulfonylpiperidin-4-ylmethyl)amine (0.18 grams, 0.45 mmole), morpholine (0.04 grams, 0.45 mmol) and diisopropylethylamine (0.12 grams, 0.93 mmole) in tetrahydrofuran (10 ml) was stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was partitioned between dichloromethane and water. The organic layer was dried over potassium carbonate and evaporated to give a residue, which was purified by flash chromatography on silica gel using 40% ethyl acetate in hexane. Appropriate fractions were combined and evaporated to give (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(morpholine-4-sulfonyl)-piperidin-4-ylmethyl]amine as an oil, (0.17 g, 85%), M+H 452. Analysis % of the hydrochloride salt: Found: C, 54.06; H, 7.62; N, 8.24. Requires: C, 54.01; H, 8.00; N, 8.22.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over potassium carbonate
  4. customevaporated
  5. customto give a residue, which
  6. customwas purified by flash chromatography on silica gel using 40% ethyl acetate in hexane
  7. customevaporated

출처 및 근거

ORD 기록
ord-a2d838cd9f124979bc4475366fd44e88
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06319920B1

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