Sodium hydride → Sodium 2-[(1-Cyclohexyl-3-azetidinyl)oxy]-3-pyridine carboxylate

HRID 4784

Reaction equation

[CH:1]1([N:7]2[CH2:10][CH:9]([OH:11])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:13]1[N:21]=[CH:20][CH:19]=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].[H-].[Na+:23]>CN(C)C=O>[CH:1]1([N:7]2[CH2:8][CH:9]([O:11][C:13]3[C:14]([C:15]([O-:17])=[O:16])=[CH:18][CH:19]=[CH:20][N:21]=3)[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na+:23]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 105 g (0.68 mole) of 1-cyclohexyl-3-azetidinol and 106 g (0.68 mole) of 2-chloronicotinic acid in 400 ml of dry dimethylformamide was added at a rapid drop to 52 g (1.35 mole) of 60% sodium hydride/mineral oil suspended in 400 ml of dry dimethylformamide at 60° C. Mild exothermic reaction was noted. After stirring for 2 hr at 60° C., the mixture was filtered. The filter cake was washed with ethylacetate and dried at 80° C./2 mm to give 174 g (86%) of crude title compound.

Workup

customMild exothermic reaction
filtrationthe mixture was filtered
washThe filter cake was washed with ethylacetate
customdried at 80° C./2 mm

Sources & evidence

ORD record: ord-a745416737d6407f8a23a934d3424d3d
Source dataset: uspto-grants-1988_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04727152

Linked notes

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