Morpholine → HCID 18960596, compound

HRID 1708064Notes

Reaction equation

HRID 1708064 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[CH3:11].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>C1COCC1>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:8])=[CH:4][C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 821314-Bromo-3-methylbenzoic acid

Product 1

HCID 18960596HCID 18960596, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-bromo-3-methylbenzoic acid (5.00 g) in dry THF (60 ml) was added dropwise at -5° to +5° to 1,1'-carbonylbis[1H-imidazole](4.90 g) and stirred under nitrogen over 10 min. Stirring was continued at +23° for 4 h, and morpholine (6.1 ml) added dropwise over 1 min. After 16 h the solution was evaporated, treated with aqueous 2M hydrochloric acid (80 ml), and extracted with ethyl acetate (4×75 ml). The combined, dried organic extracts were washed with aqueous saturated sodium bicarbonate (100 ml), dried and evaporated. A solution of the residual oil in dichloromethane (60 ml) was adsorbed onto silica gel (Merck 7734) and the mixture applied as a plug to a flash column of silica gel (Merck 9385). Gradient elution with ethyl acetate:hexane (3:7→6:4) afforded the title compound as a cream solid (5.75 g).

Workup

  1. stirringStirring
  2. waitwas continued at +23° for 4 h
  3. customAfter 16 h the solution was evaporated
  4. additiontreated with aqueous 2M hydrochloric acid (80 ml)
  5. extractionextracted with ethyl acetate (4×75 ml)
  6. washdried organic extracts were washed with aqueous saturated sodium bicarbonate (100 ml)
  7. customdried
  8. customevaporated
  9. washGradient elution with ethyl acetate:hexane (3:7→6:4)

Sources & evidence

ORD record
ord-ad8496056950454daee9092ba6b4e96a
Source dataset
uspto-grants-1994_10
Patent number
US05356893

Reaction notes

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