N-Aminomorpholine → 2-Hydroxy-N-(4-morpholinyl)-2-phenyl-2-(3-pyridinyl)-acetamide

HRID 22240노트

반응식

HRID 22240 반응식
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:5])=O.O.ON1C2C=CC=CC=2N=N1.[NH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(=O)(O)[O-].[Na+]>O1CCOCC1.CN(C)C=O>[OH:1][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[C:3]([NH:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[O:5]

참가 물질

7

반응물 4

HCID 20315N-AminomorpholineHCID 516892Sodium BicarbonateHCID 27960291-Hydroxybenzotriazole hydrateHCID 105613762-Hydroxy-2-phenyl-2-(3-pyridinyl)acetic acid

생성물 1

HCID 99487092-Hydroxy-N-(4-morpholinyl)-2-phenyl-2-(3-pyridinyl)-acetamide수율 83.4%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 312751,4-Dioxane용매

실험 절차

A mixture of 2-hydroxy-2-phenyl-2-(3-pyridinyl)acetic acid (3.48 g, 0. 015 mole) , 1-hyrdoxybenzotriazole hydrate (4.10 g, 0.03 mole), 1,3-Dicyclohexycarbodiimide (3.09 g, 0.015 mole), 4-aminomorpholine (1.45 ml, 0.015 mole), sodium bicarbonate (1.26 g, 0.015 mole), N,N-dimethyformamide (36 ml) and dioxane (36 ml) were stirred at room temperature overnight. The volatiles were removed in vacuo, dichloromethane (170 ml) was added and following filtration, the organic layer was washed with saturated sodium bicarbonate and brine. After drying, filtration and concentration, the residue was purified by column chromatography using 10% methanol in chloroform to give 3.92 g of the product as a white foam. High Res. Mass Spec. Calcd. for C17H19N3O3 :314.1505 (M+H). Found: 314.1501.

후처리

  1. customThe volatiles were removed in vacuo, dichloromethane (170 ml)
  2. additionwas added
  3. filtrationfiltration
  4. washthe organic layer was washed with saturated sodium bicarbonate and brine
  5. customAfter drying
  6. filtrationfiltration and concentration
  7. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-eb69e07ce28f4f7c848e864fd55145cd
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428035

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