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

HRID 2110122Notes

Reaction equation

HRID 2110122 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-8f33f4eea72443b0a65a1195ca8a5195
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

Loading…