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

HRID 235252Notes

Reaction equation

HRID 235252 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-11a57dd3ae67412da315bad308828e2e
Source dataset
uspto-grants-1997_01
Patent number
US05597916

Reaction notes

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