4-Methylmorpholine → HCID 86754113, compound

HRID 1416425Notes

Reaction equation

HRID 1416425 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.CN1C[CH2:21][O:20]CC1.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25].C1C[O:34]CC1>>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=1.[CH2:27]([O:26][C:24]([O:34][C:21]([O:13][CH2:11][CH:10]([CH3:9])[CH3:14])=[O:20])=[O:25])[CH:28]([CH3:30])[CH3:29]

Participants

5

Reactant 4

HCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 62365Isobutyl chloroformateHCID 8216924-(2-Pyridyl)Benzoic Acid

Product 1

HCID 86754113HCID 86754113, compound

Procedure

With the exclusion of air, 6.0 g (30 mmol) of 4-(pyridin-2-yl)-benzoic acid are suspended at -20° C. in 90 ml of THF, and 9.90 ml (90 mmol) of N-methyl-morpholine and 4.32 ml (33 mmol) of isobutyl chloroformate are added. After 30 min the mixture is filtered and washed with a small amount of cold THF; the filtrate is partially concentrated by evaporation and the residue is diluted with methylene chloride, washed with ice-water and cold brine, dried (Na2SO4) and concentrated by evaporation to yield the title compound: 1H-NMR (CDCl3) inter alia 8.75 (m, 1H), 8.16 (AB, J=8, 4H), 7.81 (m, 2H), 7.32 (4-line system, J=5, 1H), 4.16 (d, J=7, 2H), 2.10 (9-line system, J=7, 1H), 1.02 (d, J=7, 6H).

Workup

  1. filtrationAfter 30 min the mixture is filtered
  2. washwashed with a small amount of cold THF
  3. concentrationthe filtrate is partially concentrated by evaporation
  4. additionthe residue is diluted with methylene chloride
  5. washwashed with ice-water and cold brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c53570858c764d4ca48e843bfab0372f
Source dataset
uspto-grants-1999_06
Patent number
US05912352

Reaction notes

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