Water → 1-[3-(3,4-dichlorophenyl)-4-[N-(2-methoxyethyl)-3-isopropoxyphenylacetamido]-butyl]-4-phenyl-1-azoniabicyclo[2.2.2]octane chloride

HRID 1489640Notes

Reaction equation

HRID 1489640 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH2:11][C:12]([N:14]([CH2:19][CH:20]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[CH:29]=2)[CH2:21][CH2:22]OS(C)(=O)=O)[CH2:15][CH2:16][O:17][CH3:18])=[O:13])[CH:8]=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[C:36]1([C:42]23[CH2:49][CH2:48][N:45]([CH2:46][CH2:47]2)[CH2:44][CH2:43]3)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C)C=O>[Cl-:34].[Cl:35][C:30]1[CH:29]=[C:28]([CH:20]([CH2:19][N:14]([CH2:15][CH2:16][O:17][CH3:18])[C:12](=[O:13])[CH2:11][C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:6]=2)[CH2:21][CH2:22][N+:45]23[CH2:48][CH2:49][C:42]([C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)([CH2:43][CH2:44]2)[CH2:47][CH2:46]3)[CH:33]=[CH:32][C:31]=1[Cl:34]

Participants

5

Reactant 3

HCID 962WaterHCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 19705331N-(3-isopropoxyphenylacetyl)-N-(2-methoxyethyl)-2-(3,4-dichlorophenyl)-4-mesyloxybutylamine

Product 1

HCID 197053131-[3-(3,4-dichlorophenyl)-4-[N-(2-methoxyethyl)-3-isopropoxyphenylacetamido]-butyl]-4-phenyl-1-azoniabicyclo[2.2.2]octane chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2 g of the product prepared in step 5 and 1 g of 4-phenylquinuclidine are dissolved in 2 ml of dimethylformamide and the reaction mixture is heated at 80° C. for 4 hours. After cooling, the reaction mixture is poured into water and then successively extracted with ethyl acetate, washed with a 5% solution of hydrochloric acid, with a saturated solution of NaCl, dried over Na2SO4 and concentrated under vacuum.

Workup

  1. temperatureAfter cooling
  2. extractionsuccessively extracted with ethyl acetate
  3. washwashed with a 5% solution of hydrochloric acid, with a saturated solution of NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9350140ef6ec46869a95029f3c76cfa7
Source dataset
uspto-grants-1997_10
Patent number
US05679693

Reaction notes

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