Potassium Carbonate → 2-(1-Benzyl-4-piperidinylamino)-6-fluorobenzoic acid

HRID 266840Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH2:7][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.Cl[C:22]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=1[C:24]([OH:26])=[O:25]>CN(C)C=O>[CH2:14]([N:11]1[CH2:12][CH2:13][CH:8]([NH:7][C:22]2[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:23]=2[C:24]([OH:26])=[O:25])[CH2:9][CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Potassium carbonate (8.9 g), 4-amino-1-benzyl-piperidine (18.5 g), cupric oxide (0.6 g) and dimethylformamide (25 ml) are added to 2-chloro-6-fluorobenzoic acid (11.3 g) and the mixture is reacted with heating at 140° C. for 6 hours. After the reaction, the solvent is concentrated and to the resulting residue are added water (200 ml) and active carbon (1 g). The mixture is refluxed for 30 minutes. After filtration, the filtrate is cooled and then adjusted to pH 8.0 with diluted hydrochloric acid. The precipitated crystal is collected by filtration and washed successively with water and methanol to give 2-(1-benzyl-4-piperidinylamino)-6-fluorobenzoic acid (7.6 g) as white powders, m.p.: 233°-236° C.

Workup

customthe mixture is reacted
customAfter the reaction
concentrationthe solvent is concentrated and to the resulting residue
additionare added water (200 ml) and active carbon (1 g)
temperatureThe mixture is refluxed for 30 minutes
filtrationAfter filtration
temperaturethe filtrate is cooled
filtrationThe precipitated crystal is collected by filtration
washwashed successively with water and methanol

Sources & evidence

ORD record: ord-2f0e803c48e34a2b90470b5f650be1b4
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05652247

Reaction notes

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