Sodium Carbonate → HCID 18403834, compound

HRID 1017688Notes

Reaction equation

HRID 1017688 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:6]=O.[F:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:6][N:27]2[CH2:26][CH2:25][N:24]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[F:17])[CH2:29][CH2:28]2)[CH:8]=[CH:9][C:10]=1[O:11][C:12]([N:14]([CH3:16])[CH3:15])=[O:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 705291-(2-Fluorophenyl)piperazineHCID 18403787HCID 18403787, compound

Product 1

HCID 18403834HCID 18403834, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolvent2×HCID 5049666Sodium triacetoxyborohydrideSolvent

Procedure

To a solution of 3-methoxy-4-(dimethylaminocarbonyloxy)benzaldehyde (1.50 g) in 1,2-dichloroethane (14 ml) was added 1-(2-fluorophenyl)piperazine (1.21 g) in 1,2-dichloroethane (13 ml) and sodium triacetoxyborohydride (2.14 g), with stirring. The reaction mixture was stirred for 4 hrs at ambient temperature, poured into saturated sodium carbonate solution (75 ml) and extracted with dichloromethane. The organic layers were combined, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was dissolved in dichloromethane and flash chromatographed (silica gel), eluting with dichloromethane, followed by 0.1, 0.2, 0.4, 0.5, 1, and 2% methanol:dichloromethane. The appropriate fractions were combined and concentrated to afford 2.03 g (78%) of product. Recrystallization from ethyl acetate gave the analytical sample, mp 130-133° C.

Workup

  1. stirringThe reaction mixture was stirred for 4 hrs at ambient temperature
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. dissolutionThe residue was dissolved in dichloromethane
  8. customflash chromatographed (silica gel)
  9. washeluting with dichloromethane
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2a4dfe2e3be74ce0a074f6314d8a8ad7
Source dataset
uspto-grants-2002_11
Patent number
US06479495B1

Reaction notes

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