Piperazine → 1-[4-(Trifluoromethyl)benzyl]piperazine

HRID 1406644Notes

Reaction equation

HRID 1406644 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C1COCC1>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 123096p-Trifluoromethylbenzyl chloride

Product 1

HCID 27828031-[4-(Trifluoromethyl)benzyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-trifluoromethylbenzyl chloride (4{15}, 5 g, 25.7 mmol, 1 equiv.), piperazine (13.3 g, 154.2 mmol, 6 equiv.), THF (56.1 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{15} (3.97 g, 67%) as a light yellow liquid. 1H-NMR (400 MHz, CDCl3): δ 7.52 (d, 2H, J=8.0 Hz), 7.40 (d, 2H, J=8.0 Hz), 3.48 (s, 2H), 2.84 (t, 4H, J=4.8 Hz), 2.36 (br s, 4H), 1.55 (br s, 1H). 13C-NMR (100 MHz, CDCl3): δ 142.4, 129.1 (q, JC-F=32.1 Jz) 129.1 (br), 125.0 (br), 124.1 (q, JC-F=338.0 Hz), 62.9, 54.4, 45.9. 19F-NMR (375 MHz, CDCl3): δ-62.5.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{15} (3.97 g, 67%) as a light yellow liquid

Sources & evidence

ORD record
ord-f4ef5ee785944411948e5af552788924
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

Loading…