3-Phenoxybenzaldehyde → HCID 18381930, compound

HRID 2297514Notes

Reaction equation

HRID 2297514 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)(=[O:18])[CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.O.C(O)(=O)C>[C:16]([N:19]1[CH2:24][CH2:23][N:22]([CH2:11][C:10]2[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 382843-PhenoxybenzaldehydeHCID 837951-AcetylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18381930HCID 18381930, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-phenoxybenzaldehyde (1.0 g) and 1-acetylpiperazine (739 mg) were dissolved in 1,2-dichloroethane (10 ml) and sodium triacetoxyboro hydride (1.72 g) and acetic acid (300 mg) were added. The atmosphere was replaced with argon and the mixture was stirred at room temperature for 6.5 hours. Water (5 ml) and saturated sodium hydrogen carbonate (20 ml) were added and the aqueous layer was extracted 5 times with chloroform. Organic layers were combined and dried over anhydrous sodium sulfate. Chloroform was removed and the residue was purified by silica gel column chromatography (ethyl adetate-ethyl acetate:methanol=20:1-10:1) to obtain 1.32 g of 1-acetyl-4-((3-phenoxyphenyl)methyl)piperazine. Yield: 84%.

Workup

  1. extractionthe aqueous layer was extracted 5 times with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. customChloroform was removed
  4. customthe residue was purified by silica gel column chromatography (ethyl adetate-ethyl acetate:methanol=20:1-10:1)

Sources & evidence

ORD record
ord-8571f5f648524339b9c8001bfb885b64
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

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