3-Aminopropyl-4-methyl-4-phenylpiperidine → 4-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid (3-[4-methyl-4-phenyl-piperidin-1-yl)-propyl}-amide

HRID 1275208Notes

Reaction equation

HRID 1275208 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([CH3:17])([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[N+](C1C=CC([O:27][C:28]([N:30]2[CH:34]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=3)[CH2:33][O:32][C:31]2=[O:43])=O)=CC=1)([O-])=O>C1COCC1>[CH3:17][C:8]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:28]([N:30]2[CH:34]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=3)[CH2:33][O:32][C:31]2=[O:43])=[O:27])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 107996093-Aminopropyl-4-methyl-4-phenylpiperidineHCID 220490874-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidine

Product 1

HCID 867561074-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid (3-[4-methyl-4-phenyl-piperidin-1-yl)-propyl}-amideYield 74.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-amino-propyl)-4-methyl-4-phenyl-piperidine (60 mg, 0.258 mmol) in 10 mL of THF, 4-(3,4-difluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester (60 mg, 0.165 mmol) was added and the resulting yellow solution was stirred under argon atmosphere for 2 h at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc followed by MeOH:EtOAc=1:19 (Rf =0.45, MeOH:EtOAc=1:3) to obtain 4-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid {3-[4-methyl-4-phenyl-piperidin-1-yl)-propyl}-amide (56 mg, 74%). The compound was dissolved in CH2Cl2 (3 mL) and was treated with 1N HCl in ether (1 mL). The solvent was removed in vacuo to give the corresponding hydrochloride salt as a pale yellow solid. M. P. 176-178° C.; [α]D =+76.9, (c=0.23, MeOH); Anal. Calcd. For C25H30N3O3F2Cl.0.60 CH2Cl2 : C, 56.32; H, 5.94; N, 7.70. Found: C, 56.30; H, 5.80; N, 7.35.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography over silica gel with 1:1 hexane/EtOAc

Sources & evidence

ORD record
ord-cee11f035aa94246af4da7130c326047
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…