Piperazine → HCID 86681350, compound

HRID 1406642Notes

Reaction equation

HRID 1406642 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]([CH3:12])=[C:6]([CH3:13])[C:3]=1[CH2:4]Cl.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C1COCC1>[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([CH3:11])[C:7]([CH3:12])=[C:6]([CH3:13])[C:3]=1[CH2:4][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 68087Benzene, 1-(chloromethyl)-2,3,4,5,6-pentamethyl-

Product 1

HCID 86681350HCID 86681350, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Synthesized according to General Procedure A: 2,3,4,5,6-pentamethylbenzyl chloride (4{14}, 5 g, 25.4 mmol, 1 equiv.), piperazine (13.1 g, 152.5 mmol, 6 equiv.), THF (55.5 mL). Purification with flash column chromatography on silica gel (4:1 EtOAc:MeOH) afforded 5{14} (5.31 g, 85%) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 3.52 (s, 2H), 2.80 (t, 4H, J=4.8 Hz), 2.45 (br s, 4H), 2.32 (s, 6H), 2.25 (s, 3H), 2.23 (s, 6H), 1.63 (br s, 1H). 13C-NMR (125 MHz, CDCl3): δ 133.9, 133.7, 132.3, 131.9, 57.2, 54.1, 46.5, 17.0, 16.8, 16.6.

Workup

  1. customSynthesized
  2. customPurification with flash column chromatography on silica gel (4:1 EtOAc:MeOH)
  3. customafforded 5{14} (5.31 g, 85%) as a white solid

Sources & evidence

ORD record
ord-ae6d39a042b54682ad8143f12471f8d9
Source dataset
uspto-grants-2014_12
Patent number
US08916705B2

Reaction notes

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