Hydrochloric Acid → 1-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-one

HRID 2066468Notes

Reaction equation

HRID 2066468 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:21][CH2:20][C:15]4(OCC[O:16]4)[CH2:14][CH2:13]3)=[CH:8][C:6]=2[N:7]=1.Cl.[OH-].[Na+].CCOC(C)=O>O1CCOCC1>[Cl:1][C:2]1[N:3]=[C:4]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[CH2:13][CH2:14][C:15](=[O:16])[CH2:20][CH2:21]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 581170818-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane

Product 1

HCID 581171371-(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-oneYield 103.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 8-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane (0.97 g, 2.36 mmol) in 1,4-dioxane (16 mL) was slowly added concentrated HCl (24 mL) and the resulting solution was stirred at RT for 2 h. The reaction mixture was cooled to 0° C. and the pH was adjusted to 12 by careful addition of an aqueous solution of NaOH (50% w/v). EtOAc was added, the layers were separated and the aqueous layer was extracted further with EtOAc. The combined organic layers were dried (Na2SO4), then concentrated in vacuo to give the title compound as a yellow solid (0.9 g, 100%).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customthe layers were separated
  3. extractionthe aqueous layer was extracted further with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14fcd1cfa4714688996f6f699f1cd937
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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