Formaldehyde → 1-(2-Methoxyphenyl)-4-methylpiperazine

HRID 216718Notes

Reaction equation

HRID 216718 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1>ClCCCl>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH3:1])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 13461-(2-Methoxyphenyl)piperazine

Product 1

HCID 98591201-(2-Methoxyphenyl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Formaldehyde (1.84 ml in solution) is added to a solution of 1-(2-methoxyphenyl)-piperazine (4.77 g, 24.3 mmol) in 1,2-dichloroethane. NaHB(OAc)3 (7.59 g, 34 mmol) is then added portionwise. After stirring at RT overnight, the reaction is quenched by addition of a saturated solution of NaHCO3. The mixture is extracted several times with EtOAc and the combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo to afford the title compound as a colorless oil, Rt=0.615 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 207 (M+1)+.

Workup

  1. customthe reaction is quenched by addition of a saturated solution of NaHCO3
  2. extractionThe mixture is extracted several times with EtOAc
  3. washthe combined organic layers are washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-afe279f48e304265a154197c958d98f7
Source dataset
uspto-grants-2012_06
Patent number
US08193189B2

Reaction notes

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