Trifluoroacetic acid → 4-(3,4-Dichlorophenoxy)-1-(4-piperidinylmethyl)-piperidine

HRID 1727845Notes

Reaction equation

HRID 1727845 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)[CH2:8][CH2:7]1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][C:28]=1[Cl:29])[O:5][CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH:13]2[CH2:14][CH2:15][NH:16][CH2:17][CH2:18]2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 689287171-Boc-4-[4-(3,4-Dichlorophenoxy)piperidin-1-ylmethyl]piperidine

Product 1

HCID 689343214-(3,4-Dichlorophenoxy)-1-(4-piperidinylmethyl)-piperidineYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 4-[[4-(3,4-dichlorophenoxy)-1-piperidinyl]methyl]-1-piperidinecarboxylate (1.0 g) was added to a mixture of 20% TFA in dichloromethane (20 mL) and the mixture was stirred at room temperature for 1 h. Solvent was removed by evaporation and 2M sodium hydroxide solution (25 mL) was added to the residue. Product was extracted with ethyl acetate. The organic phase was washed with brine, dried, filtered and evaporated to give the title compound (0.5 g).

Workup

  1. customSolvent was removed by evaporation and 2M sodium hydroxide solution (25 mL)
  2. additionwas added to the residue
  3. extractionProduct was extracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-61bb1c8addf4444fbd1bc7f4ab93e6fa
Source dataset
uspto-grants-2009_02
Patent number
US07495013B2

Reaction notes

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