Piperazine → 1-[[4-(Trifluoromethoxy)phenyl]methyl]piperazine

HRID 1406648Notes

Reaction equation

HRID 1406648 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C1COCC1>[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 1427851-(Bromomethyl)-4-(trifluoromethoxy)benzene

Product 1

HCID 27828051-[[4-(Trifluoromethoxy)phenyl]methyl]piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-trifluoromethoxybenzyl bromide (4{17}, 5 g, 19.6 mmol, 1 equiv.), piperazine (10.1 g, 117.6 mmol, 6 equiv.), THF (42.8 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{17} (4.75 g, 93%) as a yellow liquid. 1H-NMR (500 MHz, CDCl3): δ 7.28 (d, 2H, J=8.0 Hz), 7.08 (d, 2H, J=8.0 Hz), 3.40 (s, 2H), 2.81 (t, 4H, J=5.0 Hz), 2.33 (br s, 4H), 1.51 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 148.0, 136.9, 130.1, 120.5, 120.3 (q, JC-F=255.5 Hz), 62.6, 54.3, 45.9. 19F-NMR (375 MHz, CDCl3): −58.4.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{17} (4.75 g, 93%) as a yellow liquid

Sources & evidence

ORD record
ord-8022d11964464250a513ce43db56744d
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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