Hydrochloric Acid → HCID 69843456, compound

HRID 1978047Notes

Reaction equation

HRID 1978047 reaction equation
CC1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]([CH2:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH2:23][CH:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:16][CH:15]=3)[N:9]=2)C(C)=CC=1.Cl.NO.O.Cl>C(O)C>[CH:31]1([CH2:30][N:22]([CH2:23][CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:10]3[N:9]=[C:8]([NH2:3])[CH:13]=[CH:12][CH:11]=3)=[CH:19][CH:18]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 69843587HCID 69843587, compound

Product 1

HCID 69843456HCID 69843456, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 134 mg (0.277 mmol) 2-(2,5-dimethylpyrrol-1-yl)-6-{4-[2-(bis-cyclohexylmethyl-amino)-ethyl]-phenyl}-pyridine, 96 mg (1.387 mmol) hydroxylamine hydrochloride, 1 mL water and 5 mL ethanol. The solution was heated at 80° C. for 35 h, cooled, and poured into dilute aqueous hydrochloric acid. The aqueous layer washed with ethyl acetate, the pH adjusted to 11 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 resulting oil was taken up in ether and precipitated using 1 N HCl in ether. The product was collected as a tan solid, mp 75-85° C., 68 mg (51%).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperaturecooled
  3. washThe aqueous layer washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customprecipitated
  9. customThe product was collected as a tan solid, mp 75-85° C., 68 mg (51%)

Sources & evidence

ORD record
ord-b4bddcf4c46d4629ba5b8cba6d766f1f
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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