Dichloromethane → 1-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine

HRID 605526Notes

Reaction equation

HRID 605526 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[C:16]([F:24])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(Cl)Cl>FC(F)(F)C(O)=O.ClCCl>[F:24][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:19]=[CH:18][C:17]=1[C:20]([F:22])([F:21])[F:23]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 597936284-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 597935951-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazineYield 78%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

4-(3-Fluoro-4-trifluoromethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (853 mg, 2.45 mmol) was stirred in a mixture of trifluoroacetic acid/dichloromethane (5 mL, 25% v/v) for 20 min at room temperature. The reaction mixture was combined with 25 mL of CH2Cl2 and was washed with sat'd NaHCO3 (2×10 mL) and brine. The resulting CH2Cl2 layer was dried over anhydrous Na2SO4 and was concentrated to yield crude amine. The product was further purified by silica gel chromatography (gradient eluent 0-10% MeOH in dichloromethane) to provide 4-(3-fluoro-4-trifluoromethyl-phenyl)-piperazine (473 mg, 78%). The product was used directly in step 3.

Workup

  1. washwas washed with sat'd NaHCO3 (2×10 mL) and brine
  2. dry with materialThe resulting CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationwas concentrated
  4. customto yield crude amine
  5. customThe product was further purified by silica gel chromatography (gradient eluent 0-10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-079d9115ca3b4ae4871808bba9c4768e
Source dataset
uspto-grants-2011_03
Patent number
US07915253B2

Reaction notes

Loading…