Trifluoroacetic acid → HCID 22560629, compound

HRID 1168866Notes

Reaction equation

HRID 1168866 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH2:33][CH3:34])[CH:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][C:20]([NH:26][C:27](=[O:32])[C:28]([F:31])([F:30])[F:29])=[CH:21][CH:22]=3)[CH2:17]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:33]([N:15]([CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:16]1[CH2:17][C:18]2[CH:19]=[C:20]([NH:26][C:27](=[O:32])[C:28]([F:29])([F:30])[F:31])[CH:21]=[CH:22][C:23]=2[CH2:24][CH2:25]1)[CH3:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86589088HCID 86589088, compound

Product 1

HCID 22560629HCID 22560629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the 4-({ethyl-[7-(2,2,2-trifluoro-acetylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-amino}-methyl)-piperidine-1-carboxylic acid tert-butyl ester (800 mg, 1.7 mmol) in methylene chloride (20 mL) under an inert atmosphere was added trifluoroacetic acid (5 mL) and the solution was allowed to stir at room temperature for 1 h. The reaction was concentrated in vacuo and partitioned between 10% KOH and EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated to afford N-[7-(ethyl-piperidin-4-ylmethyl-amino)-5,6,7,8-tetrahydro-naphthalen-2-yl]-2,2,2-trifluoro-acetamide as an oil which was used directly for the next step.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between 10% KOH and EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb72ad76f70d4077b08e28d6e0132e15
Source dataset
uspto-grants-2003_09
Patent number
US06627644B2

Reaction notes

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