Npc164516 → 8-Azabicyclo[3.2.1]octan-3-one hydrochloride

HRID 2086580Notes

Reaction equation

HRID 2086580 reaction equation
[Cl:1]C(OC(Cl)C)=O.C[N:9]1[CH:13]2[CH2:14][C:15]([CH2:17][CH:10]1[CH2:11][CH2:12]2)=[O:16]>ClC(Cl)C.CO>[ClH:1].[CH:10]12[NH:9][CH:13]([CH2:12][CH2:11]1)[CH2:14][C:15](=[O:16])[CH2:17]2

Participants

5

Reactant 2

HCID 79038Npc164516HCID 5213051-Chloroethyl chloroformate

Product 1

HCID 130912188-Azabicyclo[3.2.1]octan-3-one hydrochlorideYield 60.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolvent

Procedure

Add α-chloroethyl chloroformate (15.4 g, 108 mmol) to a solution of tropinone (10 g, 71.84 mmol) in dichloroethane (200 ml) dropwise at 0° C. Heat the reaction to reflux for 2 h. Evaporate the solvent to produce a brown residue. Dissolve the residue in MeOH (200 ml) and heat it to reflux for 2 h. Evaporate the MeOH and stir the solid in EtOAc, filter, collect the solid and wash with ether to give the product (7 g). Crude product was used without further purification. 1H NMR (CDCl3) δ4.45 (s, br, 2H), 3.35 (dd, 2H), 2.58 (d, 2H), 2.49 (dd, 2H), 2.0 (m, 2H).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 2 h
  4. customEvaporate the solvent
  5. customto produce a brown residue
  6. temperatureheat it
  7. temperatureto reflux for 2 h
  8. customEvaporate the MeOH
  9. filtrationfilter
  10. customcollect the solid
  11. washwash with ether

Sources & evidence

ORD record
ord-d9524fc311b944108b2cb9ce218f7c9d
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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