Trifluoroacetic acid → [1-((R)-2-amino-3-phenyl-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone

HRID 434294Notes

Reaction equation

HRID 434294 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:24])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][CH2:11]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:9][N:10]1[CH2:15][CH2:14][CH:13]([C:16]([C:17]2[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=2)=[O:24])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68809285{(R)-1-benzyl-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 68809327[1-((R)-2-amino-3-phenyl-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(R)-1-benzyl-2-[4-(4-fluoro-benzoyl)-piperidin-1-yl]-ethyl}-carbamic acid tert-butyl ester (1.12 g, 2.54 mmol) and trifluoroacetic acid (3 ml) in dichloromethane (6 ml) is stirred at ambient temperature for 3 hours. The solvent is evaporated and the residue takenup in hydrochloric acid (2M), washed with ethylacetate and basified with sodium hydroxide solution (4M) to pH8-9. The suspension is extracted with dichloromethane, the dichloromethane dried over magnesium sulphate and the solvent evaporated to afford [1-((R)-2-amino-3-phenyl-propyl)-piperidin-4-yl]-(4-fluoro-phenyl)-methanone. [MH]+341.7.

Workup

  1. customThe solvent is evaporated
  2. washthe residue takenup in hydrochloric acid (2M), washed with ethylacetate
  3. extractionThe suspension is extracted with dichloromethane
  4. dry with materialthe dichloromethane dried over magnesium sulphate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-81249c4e725740c4a9c4d5d36c7dfbca
Source dataset
uspto-grants-2003_12
Patent number
US06670379B2

Reaction notes

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