4-Phenoxybenzaldehyde → HCID 18381922, compound

HRID 2297515Notes

Reaction equation

HRID 2297515 reaction equation
[O:1]([C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][CH:9]=1)[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]([CH2:12][C:11]2[CH:14]=[CH:15][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:21][CH2:20]1)(=[O:18])[CH3:17]

Participants

8

Reactant 4

HCID 661394-PhenoxybenzaldehydeHCID 837951-AcetylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18381922HCID 18381922, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

4-phenoxybenzaldehyde (989 mg) and 1-acetylpiperazine (713 mg) were dissolved in 1,2-dichloroethane (11 ml), and sodium triacetoxyboro hydride (1.60 g) and acetic acid (300 mg) were added. The atmosphere was replaced with argon and the mixture was stirred at room temperature for 7 hours. Water (5 ml) and aqueous saturated sodium hydrogen carbonate solution (20 ml) were added and the mixture 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 acetate-ethyl acetate:methanol=20:1-10:1) to quantitatively obtain 1.55 g of 1-acetyl-4-(4-phenoxybenzyl)piperazine.

Workup

  1. extractionthe mixture 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 acetate-ethyl acetate:methanol=20:1-10:1) to quantitatively obtain 1.55 g of 1-acetyl-4-(4-phenoxybenzyl)piperazine

Sources & evidence

ORD record
ord-5e4ea4606fe447c998dbbaa082ffe94b
Source dataset
uspto-grants-2002_12
Patent number
US06492364B1

Reaction notes

Loading…