Hydrochloric Acid → HCID 12082724, compound

HRID 1977900Notes

Reaction equation

HRID 1977900 reaction equation
CC1NC(C)=CC=1C1C=C[CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([CH2:25][N:26]4[CH2:31][CH2:30][N:29]([CH2:32]CC5C=CC=CC=5)[CH2:28][CH2:27]4)=[CH:21][CH:20]=3)=[CH:15][CH:14]=2)[N:8]=1.Cl.NO.O.Cl>C(O)C>[CH2:32]([N:29]1[CH2:28][CH2:27][N:26]([CH2:25][C:22]2[CH:23]=[CH:24][C:19]([C:16]3[CH:15]=[CH:14][C:13]([C:9]4[N:8]=[C:9]([NH2:8])[CH:13]=[CH:14][CH:10]=4)=[CH:18][CH:17]=3)=[CH:20][CH:21]=2)[CH2:31][CH2:30]1)[CH2:16][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 443297Hydroxyamine hydrochloride2×HCID 54292300HCID 54292300, compound

Product 1

HCID 12082724HCID 12082724, compoundYield 135.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 100 mL round-bottomed flask equipped with N2 inlet were added 190 mg (0.361 mmol) 2-(2,5-dimethylpyrrolyl)-6-[4′-(4-phenethyl-piperazin-1-ylmethyl)-biphenyl-4-yl]-pyridine, 126 mg (1.81 mmol) hydroxylamine hydrochloride, 1 mL water, and 5 mL ethanol. The reaction was heated at reflux for 36 hours followed by treatment with an additional 50 mg hydroxylamine hydrochloride and refluxing for 24 hours. The reaction was cooled, poured into dilute aqueous hydrochloric acid, and washed with ethyl acetate. The aqueous layer was adjusted to pH 10 with 1 N sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated. The residue was converted to the hydrochloride salt using 1 N HCl in ether to afford 110 mg (55%) of a solid, mp 267-269° C.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with N2 inlet
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 36 hours
  4. temperaturerefluxing for 24 hours
  5. temperatureThe reaction was cooled
  6. washwashed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-f9f51ab54b1d4550894cd0a5388c880e
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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