Potassium Iodide → (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1910488Notes

Reaction equation

HRID 1910488 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10](=[O:27])[O:11][CH:12]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH2:2]2.[Br:28][CH2:29][CH2:30][O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[I-].[K+]>C(OCC)(=O)C>[Br-:28].[F:26][C:22]1[CH:21]=[C:20]([CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)[O:11][C:10]([NH:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][CH2:30][O:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:27])[CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 68526Benzene, (2-bromoethoxy)-2×HCID 66575633(R)-bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate

Product 1

HCID 70925887(R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 22.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(R)-Bis(3-fluorophenyl)methyl quinuclidin-3-ylcarbamate (50 mg, 0.13 mmol, prepared as in example 1) was added to a solution of (2-bromoethoxy)benzene (27.0 mg, 0.13 mmol) in ethyl acetate (2 ml). The mixture was stirred at room temperature overnight. Then (2-bromoethoxy)benzene (27 mg, 0.13 mmol) was added, and the mixture was heated at 100° C. for 15 minutes under microwave irradiation. A catalytic amount of potassium iodide was added, and the reaction was heated at 120° C. for 1 hour under microwave irradiation. The precipitate was collected by filtration and dried to obtain (R)-3-((bis(3-fluorophenyl)methoxy)carbonylamino)-1-(2-phenoxyethyl)-1-azoniabicyclo[2.2.2]octane bromide (17 mg).

Workup

  1. temperaturethe mixture was heated at 100° C. for 15 minutes under microwave irradiation
  2. temperaturethe reaction was heated at 120° C. for 1 hour under microwave irradiation
  3. filtrationThe precipitate was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-8d0c9470ab724520af1460f7460b685a
Source dataset
uspto-grants-2013_12
Patent number
US08604015B2

Reaction notes

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