Acetonitrile → 3-[2-(4-{2-Phenoxyethoxy}phenyl)ethynyl]quinuclidin-3-ol

HRID 580964Notes

Reaction equation

HRID 580964 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.Br[C:19]1[CH:29]=[C:28]([CH3:30])[C:22]([O:23]CCOC)=[C:21]([CH3:31])C=1.[C:32](#[N:34])C.Cl[CH2:36]Cl>[OH-].[Na+]>[O:9]([CH2:8][CH2:7][O:6][C:5]1[CH:16]=[CH:17][C:2]([C:31]#[C:21][C:22]2([OH:23])[CH:28]3[CH2:29][CH2:19][N:34]([CH2:32][CH2:30]3)[CH2:36]2)=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 122077041-Bromo-4-(2-phenoxyethoxy)benzeneHCID 541527811-(4-Bromo-2,6-dimethylphenoxy)-2-methoxyethane

Product 1

HCID 677403233-[2-(4-{2-Phenoxyethoxy}phenyl)ethynyl]quinuclidin-3-olYield 18%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Using a similar procedure to that described in Example 10, but using 1-(4-bromophenoxy)-2-phenoxyethane as starting material in place of 1-(4-bromo-2,6-dimethylphenoxy)-2-methoxyethane and extracting the aqueous mixture obtained after diluting the reaction mixture with 2M aqueous sodium hydroxide with dichloromethane instead of diethyl ether, there was obtained 3-[2-(4-{2-phenoxyethoxy}phenyl)ethynyl]quinuclidin-3-ol (18% yield) as a solid, m.p. 207-208° C. (after recrystallisation from acetonitrile); microanalysis, found: C,74.7; H, 6.9; N, 3.8% C23H24NO3. 0.3H2O requires: C, 74.9; H, 7.0; N, 3.8%; NMR ([CD3 ]2SO): 1.2-1.4(1H,m), 1.5-1.65(1H,m), 1.7-2.0(3H,m), 2.55-2.75(4H,t), 2.75-2.9(1H,d), 3.0-3.15(1H,d), 4.2-4.4(4H,m), 5.5(1H,s), 6.9-7.05(5H,m) and 7.2-7.4(4H,m); m/z 364 (M+H).

Workup

  1. extractionextracting the aqueous mixture
  2. customobtained
  3. customthere was obtained

Sources & evidence

ORD record
ord-841ab4fbe00142b498216084fa8308ee
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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