1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol → HCID 11635209, compound

HRID 533863Notes

Reaction equation

HRID 533863 reaction equation
[N:1]12[CH2:8][CH2:7][C:4]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[OH:10])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:23][CH2:24][CH2:25][O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=1>CC#N>[Br-:23].[OH:10][C:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]12[CH2:5][CH2:6][N+:1]([CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)([CH2:2][CH2:3]1)[CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 239923851-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanolHCID 24694511HCID 24694511, compound

Product 1

HCID 11635209HCID 11635209, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

1-Azabicyclo[2.2.2]oct-4-yl(diphenyl)methanol (30 mg, 0.102 mmol) was added to a solution of 1-{[(2-bromoethyl)oxy]methyl}-3-(methyloxy)benzene (35 mg, 0.143 mmol) in 2 CH3CN/3 CHCl3 (3 mL). The reaction was heated at 60° C. for 96 h. The reaction was concentrated, and the crude product was washed with EtOAc (3×1 mL) and then MeOH (1×1 mL). The product was dried under high vacuum to give the title compound (7.7 mg, 14%). LC/MS ESI RT 1.97 min M+458

Workup

  1. concentrationThe reaction was concentrated
  2. washthe crude product was washed with EtOAc (3×1 mL)
  3. customThe product was dried under high vacuum

Sources & evidence

ORD record
ord-57bc7554d7e544ba985837820bec5622
Source dataset
uspto-grants-2014_10
Patent number
US08853404B2

Reaction notes

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