Picolinoyl Chloride Hydrochloride → HCID 59577127, compound

HRID 2041988Notes

Reaction equation

HRID 2041988 reaction equation
Cl.[C:2]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)([CH3:5])([CH3:4])[CH3:3].Cl.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](Cl)=[O:26]>N1C=CC=CC=1>[C:2]([C:6]1[CH:17]=[CH:16][CH:15]=[CH:14][C:7]=1[O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][N:19]=2)=[O:26])[CH2:10]1)([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 53409533HCID 53409533, compound

Product 1

HCID 59577127HCID 59577127, compoundYield 43.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 3-(2-tert-butylphenoxy)pyrrolidine hydrochloride (0.26 g, 1.00 mmol) in pyridine (2.5 mL) was added picolinoyl chloride hydrochloride (0.20 g, 1.10 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure, the residue partitioned between ethyl acetate (50.0 mL) and water (50.0 mL) and separated. The organic layer was washed with saturated sodium chloride (50.0 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, 80:20 to 50:50 heptane/ethyl acetate) provided (3-(2-tert-butylphenoxy)pyrrolidin-1-yl)(pyridin-2-yl)methanone (0.14 g, 43%) as a pale yellow oil.

Workup

  1. concentrationAfter 16 h the reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate (50.0 mL) and water (50.0 mL)
  3. customseparated
  4. washThe organic layer was washed with saturated sodium chloride (50.0 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash column chromatography (silica gel, 80:20 to 50:50 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-83eb8185ef65483aadad863ff41c6b2b
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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