Hydrochloric Acid → [2-(2-Chloro-4-nitro-phenyl)-ethyl]-(4-fluoro-benzyl)-amine hydrochloride

HRID 1019734Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.Cl.O1CCOCC1>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of [2-(2-chloro-4-nitro-phenyl)-ethyl]-(4-fluoro-benzyl)-amine (3.1 g, 10 mmol) in DCM (31 mL) was added 15% HCl in dioxane (2.4 mL, 10 mmol) at 0° C. and the mixture was maintained for 1 hour at 0° C. After completion of salt formation, the volatiles were removed under reduced pressure. A mixture of 4:1 hexane and ethyl acetate (50 mL) was added to the residue and this was stirred for 15 minutes. The solvent was removed by filtration under suction and the solid was dried under reduced pressure to afford crude title product (2.8 g, 80%).

Workup

customAfter completion of salt formation, the volatiles were removed under reduced pressure
additionA mixture of 4:1 hexane and ethyl acetate (50 mL)
additionwas added to the residue
customThe solvent was removed by filtration under suction
customthe solid was dried under reduced pressure

Sources & evidence

ORD record: ord-a75c51ec56a947e98b773e94c92821f9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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