Sodium Hydroxide → HCID 69481274, compound

HRID 856064Notes

Reaction equation

HRID 856064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(Cl)Cl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][O:11][CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69480049HCID 69480049, compound

Product 1

HCID 69481274HCID 69481274, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 4-[3-(4-chlorophenyl)propoxy]-piperidine-1-carboxylate (0.151 g, 0.427 mmol) prepared in Reference example 114 was dissolved in methylene chloride (4 ml), to which trifluoroacetic acid was added, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with sodium hydroxide aqueous solution, and the mixture was extracted with methylene chloride twice. The extracts were combined and washed with brine. The organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated under reduced pressure, and the residue was dried in vacuo to afford 4-[3-(4-chlorophenyl)propoxy]piperidine (0.109 g, yield 92%) as a brown oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with methylene chloride twice
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-4c5bdfcf1adb4f2b9283d196b7e25a7a
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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