Picolinoyl Chloride Hydrochloride → (3-(2-Tert-butylphenoxy)azetidin-1-yl)(pyridin-2-yl)methanone

HRID 2041977Notes

Reaction equation

HRID 2041977 reaction equation
[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23](Cl)=[O:24]>N1C=CC=CC=1>[C:1]([C:5]1[CH:15]=[CH:14][CH:13]=[CH:12][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][N:17]=2)=[O:24])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 135033Picolinoyl Chloride HydrochlorideHCID 534095303-(2-Tert-butylphenoxy)azetidine

Product 1

HCID 59577196(3-(2-Tert-butylphenoxy)azetidin-1-yl)(pyridin-2-yl)methanoneYield 31.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an ice-cold stirred solution of 3-(2-tert-butylphenoxy)azetidine (2.00 g, 9.74 mmol) in pyridine (20.0 ml) was added picolinoyl chloride hydrochloride (2.08 g, 11.7 mmol). After stirring for 16 h at room temperature, the reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 10% aqueous Na2CO3 and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered by a pad of silica gel and concentrated under reduced pressure. The residue was purified with flash column chromatography (silica gel, 90:10 to 50:50 heptane/ethyl acetate) to provide a yellow solid. The solid was recrystallized from heptane/ethyl acetate to provide (3-(2-tert-butylphenoxy)azetidin-1-yl)(pyridin-2-yl)methanone (0.94 g, 31%) as a off-white solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 10% aqueous Na2CO3
  3. customseparated
  4. washThe organic layer was washed with saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered by a pad of silica gel
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified with flash column chromatography (silica gel, 90:10 to 50:50 heptane/ethyl acetate)
  9. customto provide a yellow solid
  10. customThe solid was recrystallized from heptane/ethyl acetate

Sources & evidence

ORD record
ord-6cbbc01115294e12bc7a14f99beb521d
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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