Trifluoroacetic acid → 6-Bromo-2-(4-piperidinyl)-1,8-naphthyridine

HRID 580906Notes

Reaction equation

HRID 580906 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[N:17][CH:18]=[C:19]([Br:24])[CH:20]=3)[N:15]=2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:24][C:19]1[CH:20]=[C:21]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[CH:23]=[CH:22]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67562152HCID 67562152, compound

Product 1

HCID 675633946-Bromo-2-(4-piperidinyl)-1,8-naphthyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of bromide 3-4 (3.5 g, 8.92 mmol), CH2Cl2 (20 ml) and TFA (10 ml) was stirred for 1.0 h. The reaction was concentrated and then azeotroped with toluene. The residue was dissolved in 1N NaOH and then extracted with CHCl3. The CHCl3 portion was washed with brine, dried (MgSO4) and concentrated providing amine 3-5 as a brown solid.

Workup

  1. concentrationThe reaction was concentrated
  2. customazeotroped with toluene
  3. dissolutionThe residue was dissolved in 1N NaOH
  4. extractionextracted with CHCl3
  5. washThe CHCl3 portion was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c6d2dd03aec94ef382b84d7c15b896a8
Source dataset
uspto-grants-1999_07
Patent number
US05919792

Reaction notes

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