Water → 1-(2-Methoxyphenyl)piperazine

HRID 1750158Notes

Reaction equation

HRID 1750158 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(O[Na])(C)(C)C.O>COCCOCCOC>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 113582-BromoanisoleHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 13461-(2-Methoxyphenyl)piperazineYield 79%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of 1-bromo-2-methoxybenzene (0.623 mL, 5.0 mmol) and piperazine (1722.8 mg, 20.0 mmol) in diglyme (5 mL) was added t-BuONa. The resulting mixture was stirred at rt for a few minutes before the addition of dichlorobis(tri-β-tolyphosphine)palladium (235.8 mg, 0.3 mmol). The resulting mixture was then stirred at 170° C. under microwave irradiation for 30 min. Water was added and the mixture was extracted with EtOAc. The combined organic layers were dried, concentrated, and purified by ISCO to give 1-(2-methoxyphenyl)piperazine (intermediate 65) (758 mg, 79%) as an off-white solid. HPLC: 95%, RT 2.641 min. MS (ESI) m/z 193.10 [M+H]+.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated
  4. custompurified by ISCO

Sources & evidence

ORD record
ord-91c41f9a929d470d8b591290f9b9a660
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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