Piperazine → 1-(4-tert-Butylbenzyl)piperazine

HRID 1406653Notes

Reaction equation

HRID 1406653 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9]Br)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C1COCC1>[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzene

Product 1

HCID 27356571-(4-tert-Butylbenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 4-tert-butylbenzyl bromide (4{20}, 4.05 mL, 22.0 mmol, 1 equiv.), piperazine (11.4 g, 132.1 mmol, 6 equiv.), THF (48.1 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{20} (3.75 g, 73%) as a beige solid. 1H-NMR (500 MHz, CDCl3): δ 7.30 (d, 2H, J=8.5 Hz), 7.22 (d, 2H, J=8.5 Hz), 3.44 (s, 2H), 2.85 (t, 4H, J=5.0 Hz), 2.38 (br s, 4H), 1.54 (br s, 1H), 1.29 (s, 9H). 13C-NMR (125 MHz, CDCl3): δ 149.6, 134.7, 128.7, 124.8, 63.1, 54.3, 45.9, 34.2, 31.2.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{20} (3.75 g, 73%) as a beige solid

Sources & evidence

ORD record
ord-61c80f69028b4082b38d04df64e0295e
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

Loading…