HCID 69479698, compound → HCID 19092281, compound

HRID 856090Notes

Reaction equation

HRID 856090 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14](C)[C:15](=O)OC(C)(C)C)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>C(Cl)Cl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:9][CH2:10][CH:11]([NH:14][CH3:15])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 69479698HCID 69479698, compound

Product 1

HCID 19092281HCID 19092281, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl N-[1-(4-chlorophenyl)piperidin-4-yl]-N-methylcarbamate (4.71 g, 14.5 mmol) prepared in Reference Example 165 was dissolved in methylene chloride (30 ml), to which trifluoroacetic acid (20 ml) was added dropwise, and the mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was then dissolved in methylene chloride. The solution was neutralized with sodium hydroxide aqueous solution, and the mixture was extracted with methylene chloride. The extract was washed with brine, dried over magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to afford N-[1-(4-chlorophenyl)piperidin-4-yl]-N-methylamine (3.1 g, yield 95%) as a pale brown oil.

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was then dissolved in methylene chloride
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-063d981b2a3240f9b4295f67def15019
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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