4-Fluorobenzonitrile → 4-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzaldehyde

HRID 1949995Notes

Reaction equation

HRID 1949995 reaction equation
N12CCC(C[OH:10])(CC1)CC2.FC1C=CC(C#N)=CC=1.[N:20]12[CH2:27][CH2:26][C:23]([CH2:28][O:29][C:30]3[CH:37]=[CH:36][C:33]([C:34]#N)=[CH:32][CH:31]=3)([CH2:24][CH2:25]1)[CH2:22][CH2:21]2>>[N:20]12[CH2:27][CH2:26][C:23]([CH2:28][O:29][C:30]3[CH:37]=[CH:36][C:33]([CH:34]=[O:10])=[CH:32][CH:31]=3)([CH2:24][CH2:25]1)[CH2:22][CH2:21]2

Participants

4

Reactant 3

HCID 145174-FluorobenzonitrileHCID 1413111-Azabicyclo(2.2.2)octane-4-methanolHCID 666269004-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzonitrile

Product 1

HCID 579343134-(1-Azabicyclo[2.2.2]oct-4-ylmethoxy)benzaldehyde

Procedure

Synthesized from (1-azabicyclo[2.2.2]oct-4-yl)methanol and 4-fluorobenzonitrile according to an analogous synthetic method to Preparation Example 15, 4-(1-azabicyclo[2.2.2]oct-4-ylmethoxy)benzonitrile (200 mg) was used according to an analogous synthetic method to Preparation Example 16 to provide the title compound (120 mg).

Workup

  1. customwas used according to an analogous synthetic method to Preparation Example 16

Sources & evidence

ORD record
ord-56844cfe624a4eb0a8246201ab341126
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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