Acetic Acid → HCID 22181078, compound

HRID 1796199Notes

Reaction equation

HRID 1796199 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[C:18](O)(=O)[CH3:19].[C:22]([BH3-])#N.[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([CH:18]([CH3:19])[CH3:22])[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydride3×HCID 22181052HCID 22181052, compound

Product 1

HCID 22181078HCID 22181078, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a suspension of 3-chloro-4-(piperidin-4-yloxy)nitrobenzene (1.50 g) obtained in reference example 8 in acetone (20 ml) were successively added acetic acid (0.33 ml) and sodium cyanoborohydride (0.18 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 4.5 hours. After stirring, to the reaction mixture was added sodium cyanoborohydride (0.18 g) and the resulting mixture was stirred at room temperature for 3 hours. After stirring, to the reaction mixture were furthermore added successively acetic acid (0.33 ml) and sodium cyanoborohydride (0.18 g), and the resulting mixture was stirred at room temperature overnight and then evaporated in vacuo. The residue obtained was neutralized with an aqueous potassium carbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to afford the title compound (1.36 g, yield: 78%) as a yellow solid.

Workup

  1. temperaturecooling
  2. stirringAfter stirring, to the reaction mixture
  3. stirringthe resulting mixture was stirred at room temperature for 3 hours
  4. stirringAfter stirring, to the reaction mixture
  5. stirringthe resulting mixture was stirred at room temperature overnight
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb9d6cdc833144adad167b553e06692b
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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