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Trifluoroacetic acid → (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine

HRID 429825
Notes
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Reaction equation

HRID 429825 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][C@@H:11]([N:13]([CH2:16][CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[CH2:14][CH3:15])[CH3:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54410775(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine

Product 1

HCID 15546287(S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amineYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-[1-(tert-butoxycarbonyl)piperidin-4-ylmethyl]amine (3.78 grams, 9.4 mmol) was added 20% trifluoroacetic acid (50 ml) in dichloromethane. The solution was stirred at room temperature for 4 hours. The solution was concentrated under reduced pressure and the residue was partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with water, dried over potassium carbonate and concentrated to give (S)-N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl-(piperidin-4-ylmethyl)amine as an oil (2.42 grams, 85%), M+H 303.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe residue was partitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic layer was washed with water
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9070073b1bef46da94f8a9537f5ca2b2
Source dataset
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06319920B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes