8-Azabicyclo(3.2.1)octane → 4-(8-Azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile

HRID 916346Notes

Reaction equation

HRID 916346 reaction equation
[CH:1]12[NH:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH2:2]2.[C:9]([C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14](F)=[CH:13][CH:12]=1)#[N:10]>N1C=CC=CC=1>[CH:5]12[N:8]([C:14]3[C:15]4[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:11]([C:9]#[N:10])=[CH:12][CH:13]=3)[CH:1]([CH2:7][CH2:6]1)[CH2:2][CH2:3][CH2:4]2

Participants

4

Reactant 2

HCID 1360978-Azabicyclo(3.2.1)octaneHCID 27367341-Cyano-4-fluoronaphthalene

Product 1

HCID 117158884-(8-Azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrileYield 4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Alternatively, the title compound was also obtained using the following procedure: 8-Azabicyclo[3,2,1]octane (20 mg, 0.18 mmol), 1-cyano-4-fluoronaphthalene (46 mg, 0.27 mmol) and pyridine (0.5 mL) were heated overnight at 100° C., concentrated in vacuo and the residue purified by preparative TLC (dichloromethane, 3× eluted) to afford the title compound (1.8 mg, 4.0%) as a yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe residue purified by preparative TLC (dichloromethane, 3× eluted)

Sources & evidence

ORD record
ord-40c01694396f40e5a0989fa1d04e863d
Source dataset
uspto-grants-2007_09
Patent number
US07268232B2

Reaction notes

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