Tetrahydrofuran → 4-Morpholinebutanenitrile

HRID 351491Notes

Reaction equation

HRID 351491 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]#[N:6].[NH:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.O1CCCC1>C(OCC)C>[O:10]1[CH2:11][CH2:12][N:7]([CH2:2][CH2:3][CH2:4][C:5]#[N:6])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 8083MorpholineHCID 214124-Bromobutyronitrile

Product 1

HCID 2945744-MorpholinebutanenitrileYield 91%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 10.0 g of 4-bromobutyronitrile, 14.7 g of morpholine and 40 g of tetrahydrofuran was heated under reflux for 10 hours. The reaction solution was cooled, diluted with diethyl ether, filtered, and concentrated in vacuum. Purification by vacuum distillation yielded 9.4 g of 4-morpholinobutyronitrile (boiling point: 85° C./50 Pa, yield: 91%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hours
  3. temperatureThe reaction solution was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customPurification
  7. distillationby vacuum distillation

Sources & evidence

ORD record
ord-b658d2c40e2545b09adf29762d0185ae
Source dataset
uspto-grants-2004_06
Patent number
US06743564B2

Reaction notes

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