Potassium Carbonate → 4-(2-{7-[4-(4-Pyridinyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}-ethoxy)benzonitrile

HRID 500508Notes

Reaction equation

HRID 500508 reaction equation
[CH:1]12[O:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([CH2:10][CH2:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1)[CH2:2]2.Cl[CH2:22][CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.BrBr>[N:29]1[CH:30]=[CH:31][C:26]([CH2:25][CH2:24][CH2:23][CH2:22][N:7]2[CH2:8][CH:1]3[O:9][CH:5]([CH2:4][N:3]([CH2:10][CH2:11][O:12][C:13]4[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=4)[CH2:2]3)[CH2:6]2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 109539414-(4-Chlorobutyl)pyridineHCID 185403754-[2-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethoxy]benzonitrile

Product 1

HCID 98014574-(2-{7-[4-(4-Pyridinyl)butyl]-9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl}-ethoxy)benzonitrileYield 57.3%

Reagents, catalysts & solvents 2

HCID 24408BromineCatalystHCID 6342AcetonitrileSolvent

Procedure

4-[2-(9-Oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethoxy]benzonitrile (0.80 g, 2.92 mmol, see preparation D above) was dissolved in MeCN (30 mL) and mixed with 4-(4-chlorobutyl)pyridine (0.74 g, 4.39 mmol, from step (i) above) and K2CO3 (1.62 g, 11.71 mmol). 1 drop of Br2 was added and the mixture was refluxed for 24 h. The mixture was filtered and evaporated. Purification by chromatography on silica, eluting with DCM:4% MeOH (satd. with ammonia), gave 0.68 g (57.2%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed for 24 h
  2. filtrationThe mixture was filtered
  3. customevaporated
  4. customPurification by chromatography on silica
  5. washeluting with DCM

Sources & evidence

ORD record
ord-ad156c6da0d34aa1ac3f91a292d93e51
Source dataset
uspto-grants-2010_08
Patent number
US07772229B2

Reaction notes

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