Chloroform → 4-[3-(4-Piperidinyl)propoxy]benzonitrile

HRID 644119Notes

Reaction equation

HRID 644119 reaction equation
C(Cl)(Cl)Cl.[C:5]([C:7]1[CH:25]=[CH:24][C:10]([O:11][CH2:12][CH2:13][CH2:14][CH:15]2[CH2:20][CH2:19][N:18](C([O-])=O)[CH2:17][CH2:16]2)=[CH:9][CH:8]=1)#[N:6].FC(F)(F)C(O)=O>O>[NH:18]1[CH2:19][CH2:20][CH:15]([CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:9]=[CH:8][C:7]([C:5]#[N:6])=[CH:25][CH:24]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 86625834HCID 86625834, compound

Product 1

HCID 592630194-[3-(4-Piperidinyl)propoxy]benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a chloroform (100 mL) solution of 14.0 g of tert-butyl=4-[3-(4-cyanophenoxy)propyl]-1-piperidinecarboxylate was dropwise added 40 mL of trifluoroacetic acid under cooling with water over a period of 10 minutes. This mixture was stirred at the same temperature for 20 minutes, and then stirred at room temperature for 35 minutes. After distilling off the solvent under reduced pressure, chloroform and water were added. A sodium hydroxide aqueous solution was added thereto for adjustment to pH 13.0. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, which was then washed with a sodium hydroxide aqueous solution and dried with potassium carbonate, followed by distilling off the solvent under reduced pressure to provide 10.3 g of 4-[3-(4-piperidinyl)propoxy]benzonitrile as pale yellow solid form.

Workup

  1. stirringstirred at room temperature for 35 minutes
  2. distillationAfter distilling off the solvent under reduced pressure, chloroform and water
  3. additionwere added
  4. additionA sodium hydroxide aqueous solution was added
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with chloroform
  7. washwhich was then washed with a sodium hydroxide aqueous solution
  8. dry with materialdried with potassium carbonate
  9. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-88f6f8316ef541f39b271d649f9975e7
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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