2-Fluorobiphenyl-4-carboxaldehyde → 3-(3-((2-Fluorobiphenyl-4-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

HRID 1678319

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-].[F:16][C:17]1[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:18]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>Cl.C(O)C>[ClH:1].[ClH:1].[F:16][C:17]1[CH:22]=[C:21]([CH:23]=[C:6]2[CH2:5][CH2:4][CH2:3][N:2]=[C:7]2[C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:20]=[CH:19][C:18]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

Conditions

Temperature: 85 °C

Procedure

3-(5-Ammoniopentanoyl)pyridinium chloride (150 mg, 0.60 mmol) and 2-fluorobiphenyl-4-carboxaldehyde (155 mg, 0.78 mmol) were combined in a reaction vessel and treated with ethanol (10 mL) and concentrated HCl(aq) (5 drops). The vessel was then sealed and the reaction was heated to 85° C. overnight then cooled to room temperature. The reaction mixture was then concentrated under reduced pressure then partially dissolved into hot isopropanol. This mixture was left to cool and crystals formed. The crystals were recovered by vacuum filtration, washed with fresh isopropanol, and dried under vacuum giving 92 mg (36%) of a yellow solid. LC-MS: RT=5.88 min, [M+H]+=343.1.

Workup

customThe vessel was then sealed
temperaturethen cooled to room temperature
concentrationThe reaction mixture was then concentrated under reduced pressure
dissolutionthen partially dissolved into hot isopropanol
waitThis mixture was left
temperatureto cool
customcrystals formed
filtrationThe crystals were recovered by vacuum filtration
washwashed with fresh isopropanol
customdried under vacuum

Sources & evidence

ORD record: ord-e639822e32474c44869eaf9ee34e3778
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008499B2

Linked notes

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