Toluene → 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)piperidine trifluoroacetic acid salt

HRID 2110826Notes

Reaction equation

HRID 2110826 reaction equation
[CH:1]1([C:7]([N:9]([CH2:20][CH:21]2[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]2)[CH2:10]/[C:11](/[CH3:19])=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].C1(C)C=CC=CC=1>ClCCl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[CH:1]1([C:7]([N:9]([CH2:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH2:10]/[C:11](/[CH3:19])=[CH:12]/[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acid2×HCID 688638074-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine

Product 1

HCID 688610534-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)piperidine trifluoroacetic acid saltYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)-1-t-butoxycarbonylpiperidine (1.55 g, 3.4 mmol) in dichloromethane (15 mL) stirring at room temperature under argon, was added trifluoroacetic acid (3.7 g, 32 mmol). After 1 h toluene (15 mL) was added and the mixture was evaporated under vacuum. The residue was repeatedly dissolved in dichloromethane and evaporated under vacuum to obtain a colorless gum that solidified on standing. This gum contained 4-(N-cyclohexylcarbonyl-N-(2-methyl-3-phenyl-2-(E)-propenyl)aminomethyl)piperidine trifluoroacetic acid salt (1.59 g, quantitative yield) and trace residual trifluoroacetic acid.

Workup

  1. customthe mixture was evaporated under vacuum
  2. dissolutionThe residue was repeatedly dissolved in dichloromethane
  3. customevaporated under vacuum
  4. customto obtain a colorless gum that

Sources & evidence

ORD record
ord-791781fd0ef5470b91dc3ae36f29a0f0
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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