Methanol → HCID 67382772, compound

HRID 1896290Notes

Reaction equation

HRID 1896290 reaction equation
S(Cl)(Cl)=O.[CH3:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1.[CH3:22]O>>[CH3:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[C:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 673827382-(4-Methyl-1-piperazinyl)-4-pyridineacetic acid

Product 1

HCID 67382772HCID 67382772, compoundYield 78%

Conditions

Temperature
85 °C

Procedure

Thionyl chloride (0.9 ml) was added to a solution of 2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)acetic acid (900 mg, 3.82 mmol) in MeOH (15 ml) at 0° C. The reaction mixture was heated for 4 h at 85° C. and concentrated. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 750 mg (78%) of methyl 2-(2-(4-methylpiperazin-1-yl)pyridin-4-yl)acetate as a colorless liquid.

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-8f111f233ace4f80a0ec44c3f382e551
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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