Hydrochloric Acid → N-methyl-N-[(1R)-1-phenylpropyl]-2-(4-piperidinyl)-4-thiazolecarboxamide

HRID 2043713Notes

Reaction equation

HRID 2043713 reaction equation
[CH3:1][N:2]([C@@H:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:24][CH3:25])[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[S:8][CH:9]=1)=[O:4].Cl>CCOCC.O1CCOCC1>[CH3:1][N:2]([C@@H:23]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:24][CH3:25])[C:3]([C:5]1[N:6]=[C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[S:8][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 674615141,1-Dimethylethyl 4-[4-[[methyl[(1R)-1-phenylpropyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate2×

Product 1

HCID 67461678N-methyl-N-[(1R)-1-phenylpropyl]-2-(4-piperidinyl)-4-thiazolecarboxamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 4-[4-[[methyl[(1R)-1-phenylpropyl]amino]carbonyl]-2-thiazolyl]-1-piperidinecarboxylate (i.e. the product of Example 1, Step D) (3.6 g, 8.1 mmol) was dissolved in 100 mL of ether and treated with 20 mL of 4 N HCl in dioxane. The reaction mixture was stirred at ambient temperature for 4 h during which time a precipitate formed and was collected. The mother liquid was concentrated under reduced pressure, treated with 20 mL of 4 N HCl in dioxane, stirred at ambient temperature for 1 h and concentrated under reduced pressure. The residue was combined with the previously collected precipitate, dissolved in water and washed with ether. The aqueous layer was basified with 1 N aqueous NaOH solution and extracted with ethyl acetate. The extract was dried over MgSO4 and concentrated under reduced pressure to give 2.33 g of the title compound as an orange oil suitable for use in subsequent reactions.

Workup

  1. customformed
  2. customwas collected
  3. concentrationThe mother liquid was concentrated under reduced pressure
  4. additiontreated with 20 mL of 4 N HCl in dioxane
  5. stirringstirred at ambient temperature for 1 h
  6. concentrationconcentrated under reduced pressure
  7. dissolutiondissolved in water
  8. washwashed with ether
  9. extractionextracted with ethyl acetate
  10. dry with materialThe extract was dried over MgSO4
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab063521710c42d6a71da55ffac3f133
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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