Hydrochloric Acid → 4-[2-(3,8-Diazabicyclo[3.2.1]oct-8-yl)ethoxy]benzonitrile

HRID 1743721Notes

Reaction equation

HRID 1743721 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][CH2:9][N:10]2[CH:15]3[CH2:16][CH2:17][CH:11]2[CH2:12][N:13](C(OC(C)(C)C)=O)[CH2:14]3)=[CH:5][CH:4]=1)#[N:2].Cl>C(OCC)(=O)C>[CH:15]12[N:10]([CH2:9][CH2:8][O:7][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:26][CH:25]=3)[CH:11]([CH2:17][CH2:16]1)[CH2:12][NH:13][CH2:14]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22235539Tert-butyl 8-[2-(4-cyanophenoxy)ethyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Product 1

HCID 222356414-[2-(3,8-Diazabicyclo[3.2.1]oct-8-yl)ethoxy]benzonitrileYield 73%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl 8-[2-(4-Cyanophenoxy)ethyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate (1.35 g, 3.8 mmol; from step (b) above) was dissolved in ethyl acetate (30 mL). The solution was cooled to 0° C., ethyl acetate (30 mL) saturated with gaseous HCl was added, and the resulting mixture stirred at r.t for 15 h. The solvent was evaporated before CHCl3 was added. The mixture was extracted with K2CO3 solution, separated, dried and evaporated to give 0.7 g (73%) of the title compound.

Workup

  1. customThe solvent was evaporated before CHCl3
  2. additionwas added
  3. extractionThe mixture was extracted with K2CO3 solution
  4. customseparated
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0eb0e1f6ff0345b1ab5e5787fccf8f6f
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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