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

HRID 1019734
Notes
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Reaction equation

HRID 1019734 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67465980[2-(2-Chloro-4-nitro-phenyl)-ethyl]-(4-fluoro-benzyl)-amine

Product 1

HCID 67465979[2-(2-Chloro-4-nitro-phenyl)-ethyl]-(4-fluoro-benzyl)-amine hydrochlorideYield 162.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customAfter completion of salt formation, the volatiles were removed under reduced pressure
  2. additionA mixture of 4:1 hexane and ethyl acetate (50 mL)
  3. additionwas added to the residue
  4. customThe solvent was removed by filtration under suction
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes