Morpholine → 4-Morpholinobenzonitrile

HRID 2120264Notes

Reaction equation

HRID 2120264 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1>O>[N:1]1([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12162Benzonitrile, 4-bromo-2×

Product 1

HCID 3948084-MorpholinobenzonitrileYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of morpholine (3 g, 34 mmol) and 4-bromobenzonitrile (1.95 g, 10.7 mmol) is heated at 120° C. The conversion of the 4-bromobenzonitrile is complete after 24 hours. Water (10 ml) is then 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 1.2 g of the title-compound. Yield: 65%, 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. filtrationThe precipitate is filtered off
  2. washwashed with water
  3. customdried under vacuum (30° C.)
  4. customRecrystallisation (50% aqueous ethanol) of the
  5. customdried crude product

Sources & evidence

ORD record
ord-19291e617fed4583ad289f66978b4286
Source dataset
uspto-grants-2004_02
Patent number
US06689882B2

Reaction notes

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