Hydrochloric Acid → Benzyl 2-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

HRID 70203Notes

Reaction equation

HRID 70203 reaction equation
Cl.O1CCOCC1.[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH:16]2[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18][N:17]2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH:9]=1>>[N:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH:16]2[CH2:21][NH:20][CH2:19][CH2:18][N:17]2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH:9]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 596715754-Tert-butyl 1-benzyl 2-((pyridin-3-yloxy)methyl)piperazine-1,4-dicarboxylate

Product 1

HCID 59671463Benzyl 2-((pyridin-3-yloxy)methyl)piperazine-1-carboxylate

Procedure

4 M HCl in 1,4-dioxane (6 mL, 24 mmol) was added to 4-tert-butyl 1-benzyl 2-((pyridin-3-yloxy)methyl)piperazine-1,4-dicarboxylate (77 mg, 0.18 mmol). After 12 h, the reaction mixture was concentrated under reduced pressure, dissolved in water, and basified with 1 N NaOH in water. The solution was extracted with EtOAc (3×), and the combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 40.5 mg (69%) of the title compound. LC-MS: RT=5.15 min, [M+H]+=328.1.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutiondissolved in water
  3. extractionThe solution was extracted with EtOAc (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-45f4e3d13b8f4ea3a9a2d4dc060ed70b
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Reaction notes

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