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

HRID 1678321

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-75ab2f627f15424ab020297c32ceee07
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008499B2

Linked notes

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