Hydrochloric Acid → HCID 43518885, compound

HRID 451417Notes

Reaction equation

HRID 451417 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[N:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C1COCC1>[CH3:21][C:19]1[CH:18]=[C:17]([CH3:22])[N:16]=[C:15]([NH:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[N:20]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67342807HCID 67342807, compound

Product 1

HCID 43518885HCID 43518885, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4,6-dimethyl-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester in THF (50 mL) was added dropwise at 0° C. hydrochloric acid (4 M in dioxane, 44.3 mL) and the reaction mixture was stirred for 22 hours at ambient temperature. The resulting suspension was filtered and dried. The residue was diluted with water (160 mL) and washed with ethyl acetate (130 mL). To the aqueous layer were added ethyl acetate (160 mL) and sodium carbonate (28.5 g) and it was extracted with ethyl acetate (160 mL). Drying of the combined organic layers over sodium sulfate afforded the title compound (2.15 g, 59%) as a light yellow solid.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customdried
  3. additionThe residue was diluted with water (160 mL)
  4. washwashed with ethyl acetate (130 mL)
  5. additionTo the aqueous layer were added ethyl acetate (160 mL) and sodium carbonate (28.5 g) and it
  6. extractionwas extracted with ethyl acetate (160 mL)
  7. dry with materialDrying of the combined organic layers over sodium sulfate

Sources & evidence

ORD record
ord-461ed56f77dc4e629654e002112ee685
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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