Hydrochloric Acid → 3-Benzyl-5-(3,4-dichlorophenyl)-5-[3-(4-hydroxy-4-phenylpiperid-1-yl)propyl]tetrahydro-2H-1,3-oxazin-2-one hydrochloride hemihydrate

HRID 1601908Notes

Reaction equation

HRID 1601908 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:14]([N:21]1[CH2:26][C:25]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=2)([CH2:27][CH2:28][CH2:29]OS(C)(=O)=O)[CH2:24][O:23][C:22]1=[O:43])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[I-].[K+].[ClH:46]>CN(C=O)C.CCOCC>[OH2:1].[ClH:41].[CH2:14]([N:21]1[CH2:26][C:25]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=2)([CH2:27][CH2:28][CH2:29][N:5]2[CH2:6][CH2:7][C:2]([OH:1])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:3][CH2:4]2)[CH2:24][O:23][C:22]1=[O:43])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH2:14]([N:21]1[CH2:26][C:25]([CH2:27][CH2:28][CH2:29][N:5]2[CH2:6][CH2:7][C:2]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([OH:1])[CH2:3][CH2:4]2)([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[CH:36]=2)[CH2:24][O:23][C:22]1=[O:43])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[ClH:46]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 963874-Phenylpiperidin-4-olHCID 158866793-Benzyl-5-(3,4-dichlorophenyl)-5-[3-(methanesulfonyloxy)propyl]tetrahydro-2H-1,3-oxazin-2-one

Product 1

HCID 1317200563-Benzyl-5-(3,4-dichlorophenyl)-5-[3-(4-hydroxy-4-phenylpiperid-1-yl)propyl]tetrahydro-2H-1,3-oxazin-2-one hydrochloride hemihydrate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

This compound is prepared by the procedure described in step D of EXAMPLE 8 from 1.6 g of 4-hydroxy-4-phenylpiperidine, 2 g of the compound obtained in step C of EXAMPLE 8 and 0.75 g of potassium iodide in 10 ml of DMF. The residue is chromatographed on silica H using DCM and then a DCM/MeOH mixture (96/4; v/v) as the eluent. The product obtained is taken up with a saturated solution of gaseous HCl in ether and the precipitate formed is wrung to give 1.34 g of the expected product. M.p.=125° C.

Workup

  1. customThis compound is prepared by the procedure
  2. customThe residue is chromatographed on silica H
  3. customThe product obtained
  4. customthe precipitate formed

Sources & evidence

ORD record
ord-a7300c19134f497f9fa7147c851fd0d4
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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