Sodium Carbonate → 1-(2-Fluoro-4-methoxybenzyl)-4-methylpiperazine

HRID 1035194Notes

Reaction equation

HRID 1035194 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:12][N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClC(Cl)C>[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:16]1[CH2:17][CH2:18][N:13]([CH3:12])[CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 27348732-Fluoro-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 580431071-(2-Fluoro-4-methoxybenzyl)-4-methylpiperazineYield 100.1%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

2-Fluoro-4-methoxybenzaldehyde (6.0 g, 39 mmol) was dissolved in dichloroethane (100 mL) and 1-methylpiperazine (4.5 g, 45 mmol) was added and the solution was stirred at rt for 30 minutes. Sodium triacetoxyborohydride (10 g, 47 mmol) was added in portions and the reaction mixture was stirred at rt over night. Aqueous Na2CO3 (sat.) was added to the reaction and the phases were separated. The aqueous phase were extracted twice with DCM and the combined organic phases were filtered through a phase separator and the solvent was removed by evaporation. There was obtained 9.3 g (100%) of 29A as a brown oil. 1H NMR (500 MHz, CDCl3): δ 2.28 (s, 3H), 2.30-2.70 (bm, 8H), 3.53 (s, 2H), 3.78 (s, 3H), 6.53-6.71 (m, 2H), 7.17-7.27 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred at rt over night
  2. customthe phases were separated
  3. extractionThe aqueous phase were extracted twice with DCM
  4. filtrationthe combined organic phases were filtered through a phase separator
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-9dfd578be2644388956b98bba70e017d
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

Loading…