Morpholine → HCID 43143579, compound

HRID 384464Notes

Reaction equation

HRID 384464 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[O:5][CH2:6][C:7]([OH:9])=O.Cl.CN(C)CCCN=C=NCC.O.N1(O)C2C=CC=CC=2N=N1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CN(C=O)C>[N:36]1([C:7](=[O:9])[CH2:6][O:5][C:4]2[CH:3]=[C:2]([OH:1])[CH:12]=[CH:11][CH:10]=2)[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 258541M-HYDROXYPHENOXYACETIC ACIDHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 43143579HCID 43143579, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-hydroxyphenoxy)acetic acid (246 mg) in DMF (10 mL) were added N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (336 mg), 1H-benzotriazol-1-ol hydrate (268 mg) and morpholine (153 μL) at room temperature, followed by overnight stirring at room temperature. The solution was concentrated under reduced pressure, and water was added to the residue, followed by extraction with ethyl acetate. The organic layer was washed sequentially with water and saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-95/5) to obtain 3-(2-(morpholin-4-yl)-2-oxoethoxy)phenol (305 mg).

Workup

  1. concentrationThe solution was concentrated under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=100/0-95/5)

Sources & evidence

ORD record
ord-9f770c8c4e48485d8c68d8f30466929d
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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