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

HRID 22240Notes

Reaction equation

HRID 22240 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-eb69e07ce28f4f7c848e864fd55145cd
Source dataset
uspto-grants-1995_06
Patent number
US05428035

Reaction notes

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