Dimethylformamide → 3-Fluoro-4-(morpholin-4-yl)benzonitrile

HRID 1362671Notes

Reaction equation

CN(C=O)C.[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1F)[C:10]#[N:11].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O>[F:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][C:14]=1[N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:10]#[N:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a DMF (20 mL) solution of 3,4-difluorobenzonitrile (3.00 g), morpholine (2.82 g) and potassium carbonate (5.97 g) were added, and the reaction solution was allowed to be warmed to 100° C. and agitated for 5.5 hours. Water and ethyl acetate were added to the reaction solution after confirming disappearance of the starting materials, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and 4.41 g of the title compound was obtained by condensing under reduced pressure. The physical properties of the compound are as follows.

Workup

customthe organic layer was partitioned
washAfter the obtained organic layer was washed with a saturated saline solution, it
dry with materialwas dried over anhydrous magnesium sulfate

Sources & evidence

ORD record: ord-3982d53916a34ca1ab11267852accbd4
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880009B2

Reaction notes

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