1-Methylpiperazine → 1-Methyl-4-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazine

HRID 2065515Notes

Reaction equation

HRID 2065515 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([B:9]2[O:13][C:12]([CH3:15])([CH3:14])[C:11]([CH3:17])([CH3:16])[O:10]2)[CH:6]=[CH:7][CH:8]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C1COCC1>[CH3:16][C:11]1([CH3:17])[C:12]([CH3:15])([CH3:14])[O:13][B:9]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[CH2:2][N:22]2[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]2)[O:10]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 27732832-[3-(Bromomethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 467397251-Methyl-4-{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-4-methylpiperazine was prepared by reacting 2-(3-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 mg, 0.35 mmol) with methyl piperazine (196 μl, 1.76 mmol) in THF at room temperature for 2 hours. The intermediate product was purified by flash chromatography to afford 68 mg of colorless oil.

Workup

  1. customat room temperature
  2. customfor 2 hours
  3. customThe intermediate product was purified by flash chromatography

Sources & evidence

ORD record
ord-c3f68c3dc0e84d2ea33037189ab0152d
Source dataset
uspto-grants-2012_10
Patent number
US08288536B2

Reaction notes

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