Trifluoroacetic acid → (R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetate

HRID 23956Notes

Reaction equation

HRID 23956 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:42]=[CH:41][C:13]([C:14]([NH:16][C@H:17]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:12][CH:11]=1.C1(OC)C=CC=CC=1>C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][C@H:17]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:18][NH:19][C:20]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[O:15])=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 20790086(R)-N-[2-(4-methoxybenzoylamino)-2-phenylethyl]-1-tert-butoxycarbonylpiperidine-4-carboxamide

Product 1

HCID 69592699(R)-N-[2-(4-Methoxybenzoylamino)-2-phenylethyl]piperidine-4-carboxamide trifluoroacetateYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Deprotection Method A) Trifluoroacetic acid was added to a stirring suspension of (R)-N-[2-(4-methoxybenzoylamino)-2-phenylethyl]-1-tert-butoxycarbonylpiperidine-4-carboxamide (2.0 g, 4.2 mmol), methylene chloride (20 mL), and anisole (0.5 g, 4.6 mmol) at room temperature. A solution was obtained and bubbling was observed. After 1 h, the reaction mixture was evaporated at 40° C. The residue was taken up in warm methanol, and to this stirring solution was added ether to precipitate the product. The precipitate was collected by vacuum filtration, washed with ethyl acetate, then dried under vacuum at 60° C. overnight to afford 1.9 g (92%) of a white solid

Workup

  1. customA solution was obtained
  2. custombubbling
  3. customthe reaction mixture was evaporated at 40° C
  4. additionto this stirring solution was added ether
  5. customto precipitate the product
  6. filtrationThe precipitate was collected by vacuum filtration
  7. washwashed with ethyl acetate
  8. customdried under vacuum at 60° C. overnight

Sources & evidence

ORD record
ord-c58a28d9c8ae4786b36cf8f0bf4991b6
Source dataset
uspto-grants-2005_02
Patent number
US06855715B1

Reaction notes

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