Trifluoroacetic acid → 4-(4-Bromophenoxy)piperidine

HRID 2242932Notes

Reaction equation

HRID 2242932 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 467390061-BOC-4-(4-bromophenoxy)piperidine

Product 1

HCID 126455664-(4-Bromophenoxy)piperidineYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3.5 g (9.83 mmol) of 1,1-dimethylethyl 4-[(4-bromophenyl)oxy]-1-piperidinecarboxylate, prepared in Step 4.1, in 20 ml of dichloromethane is admixed with 10 ml of trifluoroacetic acid and the solution is stirred at ambient temperature for 1 hour. It is evaporated to dryness and then the residue is taken up in 30 ml of toluene, which is evaporated again to dryness. The residue is subsequently washed with pentane and then taken up in a mixture of 60 ml of dichloromethane and 20 ml of 4N aqueous ammonia solution. It is stirred vigorously for 15 minutes and then the organic phase is decanted, dried over sodium sulfate and evaporated to dryness, to give 2.7 g of product in oil form, which is used as it is in the following step.

Workup

  1. customIt is evaporated to dryness
  2. customwhich is evaporated again to dryness
  3. washThe residue is subsequently washed with pentane
  4. additiontaken up in a mixture of 60 ml of dichloromethane and 20 ml of 4N aqueous ammonia solution
  5. stirringIt is stirred vigorously for 15 minutes
  6. customthe organic phase is decanted
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-aafde2332a844b128d4930f26c5a52e6
Source dataset
uspto-grants-2010_03
Patent number
US07674805B2

Reaction notes

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