Sodium Hydroxide → 1-(5-Chloropyrimidin-2-yl)piperidin-4-one

HRID 68793Notes

Reaction equation

HRID 68793 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:17][CH2:16][C:11]3(OCC[O:12]3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:17][CH2:16][C:11](=[O:12])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 682901798-(5-Chloropyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane

Product 1

HCID 682896071-(5-Chloropyrimidin-2-yl)piperidin-4-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 8-(5-chloropyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane (4.2 g) in 6 M aqueous HCl (50 mL) is stirred at room temperature for 60 h. The solution is cooled in ice bath and 4 M aqueous NaOH solution (90 mL) is added in portions to make the solution strongly basic (pH˜14). The mixture is extracted with dichloromethane (2×200 mL) and the combined organic layers are dried over Na2SO4, filtered and concentrated to yield the title compound.

Workup

  1. temperatureThe solution is cooled in ice bath
  2. extractionThe mixture is extracted with dichloromethane (2×200 mL)
  3. dry with materialthe combined organic layers are dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9c085edf15e415ebd1c4247be5d2954
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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