Morpholine → 3-Cyano-5-(4-fluorophenyl)-4-methyl-2-morpholinopyrrole

HRID 565440Notes

Reaction equation

HRID 565440 reaction equation
[C:1]([CH2:3][C:4](=[NH:8])OCC)#[N:2].[NH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(=O)([O-])O.[Na+].Br[CH:21]([CH3:31])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1)=O>C(O)C.NC(N1CCOCC1)=CC#N>[C:1]([C:3]1[C:21]([CH3:31])=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[NH:8][C:4]=1[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)#[N:2]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 256188Ethyl 2-cyanoethanecarboximidateHCID 516892Sodium BicarbonateHCID 130516522-Bromo-1-(4-fluorophenyl)propan-1-one

Product 1

HCID 158712973-Cyano-5-(4-fluorophenyl)-4-methyl-2-morpholinopyrroleYield 4.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 27636313-Amino-3-morpholinoacrylonitrileSolvent

Procedure

In anhydrous ethanol (10 ml) was dissolved 3-amino-3-morpholinoacrylonitrile, as prepared from ethyl 2-cyano-acetimidate (1.0 g) and morpholine (0.78 g) as in Reference Example 3, followed by addition of sodium hydrogen carbonate (0.95 g). Then, a solution of 2-bromo-4′-fluoropropiophenone (2.06 g) in ethanol was added dropwise thereto at room temperature with stirring. The mixture was refluxed for 10 minutes and, then, stirred at room temperature overnight. The separated crystal crop was collected by filtration and recrystallized from ethanol to provide the title compound as colorless crystals (0.12 g). m.p. 245-247° C.

Workup

  1. temperatureThe mixture was refluxed for 10 minutes
  2. stirringstirred at room temperature overnight
  3. filtrationThe separated crystal crop was collected by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5d75846c7ee841dbba65f3b2e16abd9a
Source dataset
uspto-grants-2001_01
Patent number
US06172102B2

Reaction notes

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