Hydrochloric Acid → 1-[2-(Trifluoromethyl)benzoyl]piperazine

HRID 1178042Notes

Reaction equation

HRID 1178042 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:25])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[CH2:10][CH2:9]1)=O)(C)(C)C.CO.Cl.Cl>>[N:11]1([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:23])([F:22])[F:24])=[O:25])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 21893726Hydrochloride methanolHCID 44203151HCID 44203151, compound

Product 1

HCID 167337841-[2-(Trifluoromethyl)benzoyl]piperazineYield 103.6%

Conditions

Temperature
0 °C

Procedure

A mixture of 4-(2-trifluoromethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester (2.1 g, 5.87 mmol) and MeOH.HCl (15 mL) was stirred for 30 minutes at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for a further 2 hrs. To complete the reaction HCl gas was then purged into the mixture (NaCl+H2SO4) at 0° C. for 1 hr. The methanol was then evaporated. Toluene (2×20 mL) was added and evaporated. The resultant sticky mass was recrystallized from hexane to afford 1.57 g (91% yield) of piperazin-1-yl-(2-trifluoromethyl-phenyl)-methanone.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for a further 2 hrs
  3. customwas then purged into the mixture (NaCl+H2SO4) at 0° C. for 1 hr
  4. customThe methanol was then evaporated
  5. additionToluene (2×20 mL) was added
  6. customevaporated
  7. customThe resultant sticky mass was recrystallized from hexane

Sources & evidence

ORD record
ord-6444eff844f64fa7a4fae62de5edd2bd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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