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

HRID 1409743Notes

Reaction equation

HRID 1409743 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

8-(5-Chloropyrimidin-2-yl)-1,4-dioxa-8-azaspiro[4.5]decane (4.2 g) is dissolved in 6 M HCl (50 mL) and stirred at r.t. for 60 h. The solution is cooled in an ice bath and 4 M NaOH (90 mL) is added in portions to make the solution strongly basic (pH ˜14). The mixture is extracted with dichloroemethane (2×200 mL) and the combined dichloromethane layers are dried over Na2SO4, filtered and concentrated to yield the title compound. LC (method 21): tR=4.21 min; Mass spectrum (APCI): m/z=212 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-1bbf95e26f614e6390577e9b2a959ce5
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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