Morpholine → (4-Methoxy-8-methylnaphthalen-1-yl)(morpholino)methanone

HRID 1470490Notes

Reaction equation

HRID 1470490 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([OH:16])=O)=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[C:8]([CH3:13])[CH:9]=[CH:10][CH:11]=2)[C:6]([C:14]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[O:16])=[CH:5][CH:4]=1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68282059HCID 68282059, compound

Product 1

HCID 68282070(4-Methoxy-8-methylnaphthalen-1-yl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-methoxy-8-methyl-1-naphthoic acid (above Step-5 intermediate) (1 equiv) in dry DMF (8 mL) was added, EDC.HCl (1.4 equiv) and HOBt (1.4 equiv) and the mixture was stirred for 10 min. To this, morpholine (1.5 equiv) and DIPEA (3 equiv) were added and the reaction mixture was stirred overnight. It was quenched with water (20 mL) and the aqueous layer was extracted with EtOAc (4×20 mL). The combined organic layer was washed with water (20 mL), 5% NaHCO3 solution (20 mL), brine (25 mL), dried (Na2SO4) and filtered. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography to furnish the title compound.

Workup

  1. additionwas added
  2. customIt was quenched with water (20 mL)
  3. extractionthe aqueous layer was extracted with EtOAc (4×20 mL)
  4. washThe combined organic layer was washed with water (20 mL), 5% NaHCO3 solution (20 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was evaporated under reduced pressure
  8. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8f06192d3b80413aa1d63999ca9bdd2a
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

Loading…