Hydrogen Bromide → HCID 178439627, compound

HRID 428636Notes

Reaction equation

HRID 428636 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH:12]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[CH2:13][CH3:14])=[CH:5][CH:4]=1.Br.[OH-].[NH4+]>O>[NH:18]1[CH:19]=[C:15]([CH:12]([CH:9]2[C:10]3[C:6](=[CH:5][CH:4]=[C:3]([OH:2])[CH:11]=3)[CH2:7][CH2:8]2)[CH2:13][CH3:14])[N:16]=[CH:17]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 178439628HCID 178439628, compound

Product 1

HCID 178439627HCID 178439627, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 4-[1-(6-methoxyindan-1-yl)-propyl]-1H-imidazole (174 mg) and 48% hydrobromic acid (9 ml) is heated under reflux for 50 minutes. The cooled reaction mixture is poured into water and is made basic with ammonium hydroxide solution. The product is extracted into ethyl acetate which is washed with water, dried with sodium sulfate and evaporated to dryness. The crude product is purified by flash chromatography using methylene chloride-methanol as eluent. The product is a mixture of two diastereomers (1:1).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 50 minutes
  3. customThe cooled reaction mixture
  4. extractionThe product is extracted into ethyl acetate which
  5. washis washed with water
  6. dry with materialdried with sodium sulfate
  7. customevaporated to dryness
  8. customThe crude product is purified by flash chromatography
  9. additiona mixture of two diastereomers (1:1)

Sources & evidence

ORD record
ord-7ef7832d9c704b9eb8f24da7ba010a8a
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Reaction notes

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