Hydrochloric Acid → HCID 21995450, compound

HRID 1977907Notes

Reaction equation

HRID 1977907 reaction equation
CC1NC(C)=CC=1C1C=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH2:19][CH:20]3[CH2:24][CH2:23][CH2:22][CH:21]3[N:25]([CH3:27])[CH3:26])[CH:14]=2)[N:8]=1.[CH2:29](O)[CH3:30].Cl.[NH2:33]O.Cl>O>[CH3:27][N:25]([CH3:26])[CH:21]1[CH2:22][CH2:23][CH2:24][CH:20]1[CH2:19][C:15]1[CH:14]=[C:13]([C:9]2[N:8]=[C:30]([NH2:33])[CH:29]=[CH:11][CH:10]=2)[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 443297Hydroxyamine hydrochloride2×HCID 54354482HCID 54354482, compound

Product 1

HCID 21995450HCID 21995450, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 140 mg (0.375 mmol) 2-(2,5-dimethylpyrrolyl)-6-[3-(2-dimethylamino-cyclopentylmethyl)-phenyl]-pyridine, 9 mL ethanol, 1 mL water, and 261 mg (3.75 mmol) hydroxylamine hydrochloride. The reaction was refluxed 24 hours treated with additional hydroxylamine hydrochloride, and refluxed a further 12 hours. It was then cooled, poured into dilute aqueous hydrochloric acid, and washed with ethyl acetate. The aqueous layer was adjusted to pH 10 with 6N sodium hydroxide solution, and extracted with two portions of ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and evaporated. The resulting oil (109 mg, 98.5%) was converted to the hydrochloride salt using 1N HCl in ether to afford 115 mg (83%) of a white solid, mp 60-80° C.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 24 hours
  3. temperaturerefluxed a further 12 hours
  4. temperatureIt was then cooled
  5. washwashed with ethyl acetate
  6. extractionextracted with two portions of ethyl acetate
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-6285b9511ca443b98ad275e3ab38d3d9
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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