3-Amino-propyl-4,4-diphenyl piperidine → HCID 54285979, compound

HRID 1167697Notes

Reaction equation

HRID 1167697 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.[N+](C1C=CC([O:32][C:33]([N:35]2[CH:39]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[C:42]([Cl:47])[CH:41]=3)[CH2:38][O:37][C:36]2=[O:48])=O)=CC=1)([O-])=O>C1COCC1>[C:11]1([C:8]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:33]([N:35]3[CH:39]([C:40]4[CH:45]=[CH:44][C:43]([F:46])=[C:42]([Cl:47])[CH:41]=4)[CH2:38][O:37][C:36]3=[O:48])=[O:32])[CH2:6][CH2:7]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 101085183-Amino-propyl-4,4-diphenyl piperidineHCID 22993496HCID 22993496, compound

Product 1

HCID 54285979HCID 54285979, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-propyl-4,4-diphenyl piperidine (0.04 g, 0.1 mmol) in 5 mL of THF was added 4-(3-chloro-4-fluorophenyl)-2-oxo-oxazolidine-3-carboxylic acid-4-nitro-phenyl ester (0.04 g, 0.12 mmol) and the resulting yellow solution was stirred under argon atmosphere for 3 h at room temperature. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 50% hexane/EtOAC followed by 5% MeOH in EtOAC as the eluting systems (Rf=0.45, 1:3 MeOH/EtOAC) to obtain 4-(3-Chloro-4-fluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid [3-(4,4-diphenyl-piperidin-1-yl)-propyl]-amide as white foam (wt=0.03 g). It was converted into its hydrochloride salt. M.P. 112-115° C.; Anal. Calcd. for C30H32N3O 3Cl2F.0.5 CHCl3: C, 57.95; H, 5.18; N, 6.65. Found: C, 58.06; H, 5.74; N, 6.30.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography over silica gel with 50% hexane/EtOAC

Sources & evidence

ORD record
ord-7abc280ebb0644b7b690b4af81ac0f6b
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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