Trifluoroacetic acid → 1-(2-(4-Aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one

HRID 1667164Notes

Reaction equation

HRID 1667164 reaction equation
[O:1]=[C:2]1[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][N:3]1[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([NH:29]C(=O)OC(C)(C)C)[CH2:25][CH2:24]1)=[O:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:29][CH:26]1[CH2:27][CH2:28][N:23]([C:21](=[O:22])[CH2:20][N:3]2[CH2:4][CH2:5][CH2:6][C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:2]2=[O:1])[CH2:24][CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67443748HCID 67443748, compound

Product 1

HCID 673590361-(2-(4-Aminopiperidin-1-yl)-2-oxoethyl)-3,3-diphenylpiperidin-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from Example 87A was dissolved in methylene chloride (5 mL) and treated with trifluoroacetic acid (2 mL) at room temperature for 1 hour. Then the reaction mixture was concentrated, partitioned between methylene chloride and an aqueous solution of sodium bicarbonate. The organic layer was separated, dried over magnesium sulfate, and concentrated to yield the title compound. MS (ESI+) m/z 391 (M+H)+.

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. custompartitioned between methylene chloride
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec506fc63b2b446b89268750f02f3281
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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