4-Methylmorpholine → (4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

HRID 2053752Notes

Reaction equation

HRID 2053752 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([CH3:11])[CH:3]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=[CH:23][CH:24]=[CH:25][C:20]=2[N:19]=N1.CN1CCOCC1.N1CC=CC1>CN(C)C=O>[N:19]1([C:6]([C:5]2[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][C:4]=2[CH3:11])=[O:8])[CH2:20][CH:25]=[CH:24][CH2:23]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 660593-PyrrolineHCID 995704-Bromo-2-methylbenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

25.0 g (0.12 mol) of 4-bromo-2-methylbenzoic acid is dissolved in 250 mL of dimethylformamide and after the addition of 41.7 g (0.13 mol) of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 14.3 mL (0.13 mol) of N-methylmorpholine and 9.6 mL (0.12 mol) of 2,5-dihydropyrrole, the mixture is stirred for 16 hours at ambient temperature. Then it is poured onto ice water and extracted with ethyl acetate. The combined organic extracts are washed with sodium hydrogen carbonate solution, dried over sodium sulfate and concentrated by evaporation. Yield: 31.6 g (97% of theory); Rf value: 0.45 (silica gel; dichloromethane/ethanol=19:1).

Workup

  1. additionThen it is poured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts are washed with sodium hydrogen carbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-13068a93f2ec4ec2ac10d0c3f94f8be7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…