3-Fluorobenzoic Acid → Rac-n-[1-(3,4-dichloro-phenyl)-ethyl]-3-fluoro-benzamide

HRID 1677113Notes

Reaction equation

HRID 1677113 reaction equation
Cl.CN(C)CCCN=C=NCC.[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]([NH2:23])[CH3:22])[CH:17]=[CH:18][C:19]=1[Cl:20].[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]([NH:23][C:28](=[O:29])[C:27]2[CH:31]=[CH:32][CH:33]=[C:25]([F:24])[CH:26]=2)[CH3:22])[CH:17]=[CH:18][C:19]=1[Cl:20]

Participants

6

Reactant 3

HCID 99683-Fluorobenzoic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 31592421-(3,4-dichlorophenyl)ethanamine

Product 1

HCID 24396994Rac-n-[1-(3,4-dichloro-phenyl)-ethyl]-3-fluoro-benzamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 143.8 mg (0.75 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC.HCl) and 91.6 mg (0.75 mmol) 4-dimethylaminopyridine (DMAP) in 1.5 ml dichloromethane were added 142 mg (0.75 mmol) rac-1-(3,4-dichloro-phenyl)-ethylamine and the solution stirred at ambient temperature for 5 min. To this solution were added 70 mg (0.5 mmol) 3-fluoro-benzoic acid and the mixture stirred at ambient temperature for 5 hours.

Workup

  1. stirringthe mixture stirred at ambient temperature for 5 hours

Sources & evidence

ORD record
ord-6adb2804bd084203a37132ff66fd7bdd
Source dataset
uspto-grants-2011_08
Patent number
US08008305B2

Reaction notes

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