Trifluoroacetic acid → HCID 22622405, compound

HRID 840414Notes

Reaction equation

HRID 840414 reaction equation
O=[CH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N)(OC(C)(C)C)=[O:17].FC(F)(F)C(O)=O>C(Cl)Cl>[C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:17])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86757921HCID 86757921, compound

Product 1

HCID 22622405HCID 22622405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(2-oxoethylphenyl)-piperidine-N-Boc-amine was stirred in a solution of DCM (3 mL) and trifluoroacetic acid (1 mL) for 1 h, concentrated under reduced pressure, residual solvent was coevaporated twice from methanol, and dried under high vacuum to provide the N-deprotected 4-(2-acetylphenyl)piperidine. Using standard reductive amination conditions 4-(2-acetylphenyl)piperidine was reacted with N-[2-(S)-(3,4-dichlorophenyl)-4-oxobutyl]-N-methyl-3-cyano-1-naphthamide and converted to the citrate salt. MS m/z 612 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure, residual solvent
  2. customdried under high vacuum

Sources & evidence

ORD record
ord-bf19c6a3b1ff471db6b5707cc55de856
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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