Water → 3-Benzyl-5-(3,4-dichlorophenyl)-5-[3-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]propyl]tetrahydro-2H-1,3-oxazin-2-one chloride hemihydrate

HRID 849342Notes

Reaction equation

HRID 849342 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][N:10]([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:15]([N:22]1[CH2:27][C:26]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)([CH2:28][CH2:29][CH2:30]OS(C)(=O)=O)[CH2:25][O:24][C:23]1=[O:44])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[OH2:24].[Cl-:42].[CH2:15]([N:22]1[CH2:27][C:26]([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)([CH2:28][CH2:29][CH2:30][N+:10]23[CH2:13][CH2:14][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([CH2:8][CH2:9]2)[CH2:12][CH2:11]3)[CH2:25][O:24][C:23]1=[O:44])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH2:15]([N:22]1[CH2:27][C:26]([CH2:28][CH2:29][CH2:30][N+:10]23[CH2:13][CH2:14][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)([CH2:8][CH2:9]2)[CH2:12][CH2:11]3)([C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=2)[CH2:25][O:24][C:23]1=[O:44])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-:42]

Participants

5

Reactant 3

HCID 962WaterHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 158866793-Benzyl-5-(3,4-dichlorophenyl)-5-[3-(methanesulfonyloxy)propyl]tetrahydro-2H-1,3-oxazin-2-one

Product 1

HCID 1317200573-Benzyl-5-(3,4-dichlorophenyl)-5-[3-[4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl]propyl]tetrahydro-2H-1,3-oxazin-2-one chloride hemihydrateYield 121%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.2 g of 4-phenyl-1-azabicyclo-[2.2.2]octane and 2 g of the compound obtained in step C of EXAMPLE 8 in 10 ml of DMF is heated at 50° C. for 3 hours. After cooling to RT, the reaction mixture is poured into water and extracted with DCM, the organic phase is washed with water, with saturated NaCl solution, twice with 2 N HCl solution, twice with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is taken up with AcOEt and the precipitate formed is wrung to give 1.56 g of the expected product. M.p.=235° C.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with DCM
  3. washthe organic phase is washed with water, with saturated NaCl solution, twice with 2 N HCl solution, twice with water and with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. customthe solvent is evaporated off under vacuum
  6. customthe precipitate formed

Sources & evidence

ORD record
ord-cf2a27da4e0a408cbc365def9f64e4cb
Source dataset
uspto-grants-2000_01
Patent number
US06011154

Reaction notes

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