Morpholine → 4-Morpholinobenzonitrile

HRID 2120265Notes

Reaction equation

HRID 2120265 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.FC(F)(F)S([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)(=O)=O>O>[N:1]1([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 27778244-(Trifluoromethylsulphonyl)benzonitrile2×

Product 1

HCID 3948084-MorpholinobenzonitrileYield 52%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of morpholine (3 g, 34 mmol) and the freshly prepared 4-[(trifluoromethyl)sulfonyl] benzonitrile (1.2 g, 5.1 mmol, Ref.: A. M. Echavarren and J. K. Stille, J. Am. Chem. Soc. 1987, 109, 5478-5486.), is heated at 120° C. The conversion of the 4-[(trifluoromethyl)sulfonyl]benzonitrile is complete after 20 hours. Water (10 ml) is than added into the reaction mixture. The precipitate is filtered off, washed with water and dried under vacuum (30° C.). Recrystallisation (50% aqueous ethanol) of the dried crude product gives 0.5 g of the title-compound. Yield: 52%, m.p. 82-83° C.; MS 188 (100, M+); H1 NMR (CDCl3): δ 7.46 (dd, 2H), 6.81 (dd, 2H), 3.79 (t, 4H), 3.22 (t, 4H); C13 NMR (CDCl3): δ 153.69, 133.71, 120.07, 114.26, 101.16, 66.65, 47.49.

Workup

  1. additionthan added into the reaction mixture
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customdried under vacuum (30° C.)
  5. customRecrystallisation (50% aqueous ethanol) of the
  6. customdried crude product

Sources & evidence

ORD record
ord-e2b9047224d84ccc89a20d087025ae92
Source dataset
uspto-grants-2004_02
Patent number
US06689882B2

Reaction notes

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