Piperazine → 1-Biphenyl-2-ylmethyl-piperazine

HRID 1406638Notes

Reaction equation

HRID 1406638 reaction equation
[C:1]1([C:7]2[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=2[CH2:9]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>C1COCC1>[C:7]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH2:9][N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 2633651-(Bromomethyl)-2-phenylbenzene

Product 1

HCID 183819371-Biphenyl-2-ylmethyl-piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 2-phenylbenzyl bromide (4{12}, 5 g, 20.2 mmol, 1 equiv.), piperazine (10.5 g, 121.4 mmol, 6 equiv.), THF (44.2 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{12} (3.92 g, 77%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.55 (dd, 1H, J=1.5, 7.0 Hz), 7.42-7.38 (m, 4H) 7.36-7.32 (m, 2H), 7.30 (dd, 1H, J=1.5, 7.0 Hz), 7.27 (dd, 1H, J=1.5, 7.0 Hz), 3.40 (s, 2H), 2.83 (t, 4H, J=5.0 Hz), 2.33 (br s, 4H), 1.58 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 142.6, 141.4, 135.5, 129.9, 129.8, 129.4, 127.8, 126.9, 126.7, 126.6, 60.3, 54.1, 46.1.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{12} (3.92 g, 77%) as a white solid

Sources & evidence

ORD record
ord-14224e29ea074cc084d94a6b8c277d00
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

Loading…