Piperazine → HCID 18770224, compound

HRID 1406657Notes

Reaction equation

HRID 1406657 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH2:8]Br)([CH3:4])([CH3:3])[CH3:2].[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH2:8][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 44475071-(Bromomethyl)-3,5-di-tert-butylbenzene

Product 1

HCID 18770224HCID 18770224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 3,5-di-tert-butylbenzyl bromide (4{22}, 5 g, 17.7 mmol, 1 equiv.), piperazine (9.1 g, 105.9 mmol, 6 equiv.), THF (38.7 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{22} (4.15 g, 82%) as a white solid. 1H-NMR (500 MHz, CDCl3): δ 7.31 (t, 1H, J=2.0 Hz), 7.15 (d, 2H, J=2.0 Hz), 3.51 (s, 2H), 2.89 (t, 4H, J=5.0 Hz), 2.42 (br s, 4H), 1.73 (br s, 1H), 1.33 (s, 18H). 13C-NMR (125 MHz, CDCl3): δ 150.3, 136.8, 123.3, 120.7, 64.1, 54.3, 46.1, 34.7, 31.5.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{22} (4.15 g, 82%) as a white solid

Sources & evidence

ORD record
ord-b30190e57c86413289f6ecade9ab9684
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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