Potassium Iodide → 5-[2-(4-Acetamido-4-phenylpiperid-1-yl)ethyl]-3-benzyl-5-(3,4-dichlorophenyl)tetrahydro-2H-1,3-oxazin-2-one hydrochloride

HRID 849337Notes

Reaction equation

HRID 849337 reaction equation
[C:1]([NH:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].[CH2:17]([N:24]1[CH2:29][C:28]([C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([Cl:44])[CH:38]=2)([CH2:30][CH2:31]OS(C)(=O)=O)[CH2:27][O:26][C:25]1=[O:45])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[I-].[K+]>CN(C=O)C>[ClH:43].[C:1]([NH:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][CH2:7][N:8]([CH2:31][CH2:30][C:28]2([C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[C:39]([Cl:44])[CH:38]=3)[CH2:27][O:26][C:25](=[O:45])[N:24]([CH2:17][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:29]2)[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 158866683-Benzyl-5-(3,4-dichlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]tetrahydro-2H-1,3-oxazin-2-oneHCID 15886675N-(4-Phenylpiperidin-4-yl)acetamide

Product 1

HCID 212005175-[2-(4-Acetamido-4-phenylpiperid-1-yl)ethyl]-3-benzyl-5-(3,4-dichlorophenyl)tetrahydro-2H-1,3-oxazin-2-one hydrochlorideYield 52.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound is prepared by the procedure described in step D of EXAMPLE 1 from 2.77 g of 4-acetamido-4-phenylpiperidine, 1.7 g of the compound obtained in step C of EXAMPLE 1 and 0.61 g of potassium iodide in 10 ml of DMF. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (97/3; v/v) as the eluent. The residue is taken up with a saturated solution of gaseous HCl in ether and the solvent is evaporated off under vacuum to give 0.6 g of the expected product after crystallization from AcOEt. M.p.=168° C.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe residue is chromatographed on silica H
  3. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-5051340c697049188f18e14ca1fb5433
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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