Hydrochloric Acid → 2-(4-Isopropyl-piperazin-1-yl)-pyridin-4-ylamine

HRID 272535Notes

Reaction equation

HRID 272535 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[C:14]([NH:16]C(=O)C)[CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].Cl>O1CCOCC1>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68946851N-[2-(4-Isopropyl-piperazin-1-yl)-pyridin-4-yl]-acetamide

Product 1

HCID 617084702-(4-Isopropyl-piperazin-1-yl)-pyridin-4-ylamineYield 57%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.1 g (8 mmol) N-[2-(4-isopropyl-piperazin-1-yl)-pyridin-4-yl]-acetamide and 10.5 ml 4N HCl in 25 ml dioxane was heated to 100° C. for 2 h. After evaporation of all volatiles the residue was treated with water and NaHCO3 aq. sat. and extracted with DCM. The combined organic layers were washed with NaCl aq. sat., dried with MgSO4 and evaporated. The residue was triturated with DCM and dried to yield 1 g (57%) of the title compounds as white solid. MS: (m/e): 221.3 (MH+).

Workup

  1. customAfter evaporation of all volatiles the residue
  2. additionwas treated with water and NaHCO3 aq. sat.
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with NaCl aq. sat.
  5. dry with materialdried with MgSO4
  6. customevaporated
  7. customThe residue was triturated with DCM
  8. customdried

Sources & evidence

ORD record
ord-b0860360945c4b2b9b782d5e182cd6e7
Source dataset
uspto-grants-2008_11
Patent number
US07456175B2

Reaction notes

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