Morpholine → (3,5-Dimethyl-4-nitrophenyl)(morpholino)methanone

HRID 237521Notes

Reaction equation

HRID 237521 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([CH3:26])[C:22]=1[N+:23]([O-:25])=[O:24])[C:17]([OH:19])=O.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>O1CCCC1>[CH3:26][C:21]1[CH:20]=[C:16]([C:17]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[O:19])[CH:15]=[C:14]([CH3:13])[C:22]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 2494133,5-Dimethyl-4-nitrobenzoic acid

Product 1

HCID 86697183(3,5-Dimethyl-4-nitrophenyl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (1.66 g) is added to a solution of 3,5-dimethyl-4-nitrobenzoic acid (1 g) in tetrahydrofuran (10 mL). The mixture is stirred for 3 hours at room temperature, morpholine (0.9 mL) is added and the mixture is stirred for further 30 minutes. After concentration the mixture is diluted with ethyl acetate and washed with hydrochloric acid (0.2 M), saturated aqueous NaHCO3 solution and brine. The organic phase is dried (Na2SO4) and concentrated to give the title compound. Yield: 1.3 g; LC (method 20): tR=5.10 min; Mass spectrum (ESI+): m/z=265 [M+H]+.

Workup

  1. stirringthe mixture is stirred for further 30 minutes
  2. concentrationAfter concentration the mixture
  3. additionis diluted with ethyl acetate
  4. washwashed with hydrochloric acid (0.2 M), saturated aqueous NaHCO3 solution and brine
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-060d2287954b441cba86744a9869e438
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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