Acetic Acid → HCID 68852660, compound

HRID 1984688Notes

Reaction equation

HRID 1984688 reaction equation
[CH3:1][C:2]1[N:6]2[CH2:7][CH2:8]C[CH2:10][C:5]2=[N:4][CH:3]=1.[I:11]N1C(=O)CCC1=O.[C:19](O)(=O)[CH3:20]>>[CH2:7]([N:6]1[C:2]([CH3:1])=[C:3]([I:11])[N:4]=[C:5]1[CH2:10][CH2:19][CH3:20])[CH3:8]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 120273N-IodosuccinimideHCID 122610573-METHYL-5,6,7,8-TETRAHYDROIMIDAZO[1,2-A]PYRIDINE

Product 1

HCID 68852660HCID 68852660, compoundYield 84%

Procedure

To a solution of 3-methyl-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine (Eur. J. Med. Chem. 10(5), 528, 1975; 1.85 g, 13.6 mmol) in acetic acid (50 mL) was added N-iodsuccinimide (4.28 g, 19.0 mmol) and the reaction mixture was stirred for 3 h at ambient temperature. It was concentrated and the residue extracted with aqueous sodium carbonate (sat.) and ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 93:7) afforded the title compound (3.00 g, 84%) as a dark brown solid. MS: m/e=262.0 [M]+.

Workup

  1. concentrationIt was concentrated
  2. extractionthe residue extracted with aqueous sodium carbonate (sat.) and ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 93:7)

Sources & evidence

ORD record
ord-7cd75744cb9e49f5a3fcff99a2be045f
Source dataset
uspto-grants-2009_06
Patent number
US07544704B2

Reaction notes

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