5-Phenyl-2-furaldehyde → 3-(3-((5-Phenylfuran-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

HRID 1444750

Reaction equation

[Cl-:1].[NH3+:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:10]=[NH+:11][CH:12]=[CH:13][CH:14]=1)=O.[Cl-].[C:16]1([C:22]2[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)(C)C>[ClH:1].[ClH:1].[C:16]1([C:22]2[O:26][C:25]([CH:27]=[C:6]3[CH2:5][CH2:4][CH2:3][N:2]=[C:7]3[C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 85 °C

Procedure

3-(5-Ammoniopentanoyl)pyridinium chloride (188 mg, 0.75 mmol) was transferred to a reaction vessel and treated with isopropanol (12 mL). 5-Phenyl-2-furaldehyde (193 mg, 1.12 mmol) was added, the reaction vessel was sealed, and the reaction was heated to 85° C. with stirring for 6 hours. The reaction was then cooled to room temperature, and the precipitate was recovered by vacuum filtration, washed with isopropanol and ether then dried under vacuum giving 264 mg (91%) of an orange solid. LC-MS: RT=5.15 min, [M+H]+=315.1.

Workup

customthe reaction vessel was sealed
temperatureThe reaction was then cooled to room temperature
filtrationthe precipitate was recovered by vacuum filtration
washwashed with isopropanol and ether
customthen dried under vacuum

Sources & evidence

ORD record: ord-f1655f4472fc408f818e0e0d683a4319
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662965B2

Linked notes

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