Morpholine → HCID 18475738, compound

HRID 2187426Notes

Reaction equation

HRID 2187426 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:10].[F-].[K+].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>CN(C)C=O>[CH3:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 522689Potassium FluorideHCID 27374944-Bromo-3-methylbenzonitrile

Product 1

HCID 18475738HCID 18475738, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 4-bromo-3-methylbenzonitrile (11 g, 56 mmol) and potassium fluoride (3.3 g, 56 mmol) in anhydrous N,N-dimethylformamide (150 mL) was added morpholine (15 g, 170 mmol) and the reaction was heated at 145° C. for 4 days. The solvent was evaporated in vacuo and the residue was partitioned between diethyl ether and water. The phases was separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo. Purification on a silica gel column using toluene followed by chloroform as eluents gave 1.3 g (11% yield) of the title compound as white crystals: mp 85-86° C.; EIMS (70 eV) m/z (relative intensity) 202 (71, M+).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between diethyl ether and water
  3. customThe phases was separated
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customPurification on a silica gel column

Sources & evidence

ORD record
ord-254af52978764d25a2291a29606e26f9
Source dataset
uspto-grants-2002_06
Patent number
US06410530B1

Reaction notes

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