Water → HCID 20037587, compound

HRID 1904657Notes

Reaction equation

[CH3:1][C:2]1[C:3](N2CCCCC2)=[CH:4][C:5]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=O)=[N:6][CH:7]=1.O.NN.[OH-].[K+].O>C(O)COCCOCCO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)([N:6]2[CH2:7][CH2:2][CH2:3][CH2:4][CH2:5]2)[NH:6][CH:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 5-methyl-2-(1-napthoyl)-4-piperidinopyridine in 1 ml of triethylene glycol was added 30 mg of 100% hydrazine hydrate, and the mixture was stirred at 120° C. for 1.5 hours. Potassium hydroxide (42 mg) was added to the reaction mixture, and the mixture was heated at about 200° C. for 1 hour. The reaction mixture was poured into water, and extracted with ether. The ether layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluted with chloroform and then with chloroform/methanol (=50/1)] to give 5-methyl-2-(1-naphthylmethyl)-2-piperidinopyridine as an oil. The oil was treated with an ethanol solution of hydrogen chloride and recrystallized from acetone/ether to give 44 mg (yield 40%) of the captioned compound.

Workup

temperaturethe mixture was heated at about 200° C. for 1 hour
extractionextracted with ether
washThe ether layer was washed with water
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography [
washeluted with chloroform

Sources & evidence

ORD record: ord-59d000a2fd6048bca357cd47db0b232b
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04839353

Reaction notes

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