Hydrochloric Acid → 4-(1-Benzyl-4-piperidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-one

HRID 2217863Notes

Reaction equation

[CH:1]([NH:3][NH:4][C:5]([NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:6])=O.[OH-].[K+].Cl>>[C:15]1([CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([N:7]3[CH:1]=[N:3][NH:4][C:5]3=[O:6])[CH2:9][CH2:10]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 14797Potassium Hydroxide

HCID 688114854-(1-Benzylpiperidin-4-yl)-1-formylsemicarbazide

Product 1

HCID 591757344-(1-Benzyl-4-piperidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-oneYield 94.1%

Conditions

Temperature: 90 °C

Procedure

2-Formyl-N-[1-(phenylmethyl)-4-piperidinyl]-hydrazinecarboxamide (Example 64(a)) (2.5 g) was divided between S x 10 mL vials. Potassium hydroxide (5 mL, 1 M solution in methanol) was added to each vial and the reactions were heated at 90° C. for 35 minutes within a microwave. The combined products were acidified to pH6 with aqueous 2M hydrochloric acid and were then evaporated to dryness. Purification (SiO2, methanol:dichloromethane:acetic acid 15:85:1 as eluant) gave the sub-title compound as an oil (2.2 g).

Workup

customwere then evaporated to dryness
customPurification (SiO2, methanol:dichloromethane:acetic acid 15:85:1 as eluant)

Sources & evidence

ORD record: ord-d4af8a49b816457ea8804e58dd074f0d
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07408065B2

Reaction notes

Loading…