Potassium Iodide → HCID 19879235, compound

HRID 1885587Notes

Reaction equation

HRID 1885587 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[H-].[Na+].[I-].[K+].[CH2:28](Br)[CH2:29][CH3:30]>CN(C)C=O>[CH2:28]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)[CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 78401-Bromopropane2×HCID 24758Sodium hydride2×HCID 136403394HCID 136403394, compound

Product 1

HCID 19879235HCID 19879235, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 1.2 g (2.7 mmoles) of 2-(4-hydroxyphenyl) 3-(4-pyridyl)-6,7-dihydro[5H]-pyrrolo-[1,2-a]imidazole dihydrobromide of Example 10 in 20 ml of dry dimethylformamide cooled in an ice bath was treated with 360 mg (9.0 mmoles) of 60% sodium hydride dispersion and allowed to warm to room temperature. 450 mg (2.7 mmoles) of powdered potassium iodide was added, followed by dropwise addition of a solution of 332 mg (2.7 mmoles) of 1-propyl bromide in 2 ml of dimethylformamide. After 2 hours an additional 83 mg (0.67 mmole) of 1-propyl bromide was added followed by another 90 mg (2.25 mmoles) of 60% sodium hydride suspension, and the mixture heated to 65° C. for 2.5 hours. After stirring overnight, the mixture was poured into 10 volumes of ice water and extracted three times with ethyl acetate. The organic phase was washed with water, dried over anhydrous potassium carbonate and concentrated in vacuo. The residue was flash chromatographed on silica and the fractions eluting with 3 to 6% methanol in chloroform were combined, concentrated in vacuo, and recrystallized from ethyl acetate to afford the titled compound, mp 148.5°-150° C. Anal. Calcd. for C20H21N3O: C, 75.21; H, 6.63; N, 13.16. Found: C, 74.95; H, 6.59; N, 13.17.

Workup

  1. temperaturethe mixture heated to 65° C. for 2.5 hours
  2. extractionextracted three times with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica
  7. washthe fractions eluting with 3 to 6% methanol in chloroform
  8. concentrationconcentrated in vacuo
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-760c34596796495689ce51ff20105554
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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