Toluene → 4-Morpholinebutanenitrile

HRID 924627Notes

Reaction equation

HRID 924627 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.Cl[CH2:15][CH2:16][CH2:17][C:18]#[N:19]>C(Cl)(Cl)Cl>[N:1]1([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 8083MorpholineHCID 123364-Chlorobutyronitrile

Product 1

HCID 2945744-Morpholinebutanenitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

196.9 ml morpholine, 500 ml toluol and 100 ml chloroform were stirred in a round-bottomed flask under N2 atmosphere and at 80° C. After one hour 100 g 4-chlorobutyronitrile was added dropwise within one hour. The reaction was stirred one day at 80° C. and another day at room temperature. The mixture was fritted and the residue was washed two times with ether. The filtrate was concentrated and finally distilleed under vacuum. The product fractions were collected at 95-100° C. and 1.2-0.89 Torr. The purity of the colourless oil was judged by gas chromatography and 1H-NMR.

Workup

  1. washthe residue was washed two times with ether
  2. concentrationThe filtrate was concentrated
  3. customThe product fractions were collected at 95-100° C.

Sources & evidence

ORD record
ord-f1b0626b7ce64f80a3994df683477a29
Source dataset
uspto-grants-2016_03
Patent number
US09283186B2

Reaction notes

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