Hydrochloric Acid → HCID 21995458, compound

HRID 1977911Notes

Reaction equation

HRID 1977911 reaction equation
CC1NC(C)=CC=1[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:8]=1.C(O)C.Cl.[NH2:30]O.Cl>O>[NH:22]1[CH2:23][CH2:24][CH:19]([C:16]2[CH:17]=[CH:18][C:13]([C:9]3[N:8]=[C:7]([NH2:30])[CH:12]=[CH:11][CH:10]=3)=[CH:14][CH:15]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 54468976HCID 54468976, compound

Product 1

HCID 21995458HCID 21995458, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 100 mg (0.302 mmol) 4-(4-(2-(2,5-dimethylpyrrolyl)pyrid-6-yl)phenyl)piperidine, 10 mL ethanol, 1 mL water, and 417 mg (6.04 mmol) hydroxylamine hydrochloride. The reaction was refluxed 20 hours cooled, and poured into dilute aqueous hydrochloric acid, then washed with ethyl acetate. The aqueous layer was adjusted to pH 10 with 6 N sodium hydroxide solution and extracted twice with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, and evaporated. The resulting oil (77 mg, 100%) was converted to the hydrochloride salt using HCl in, ether to afford a tan solid, 32 mg (32%), mp dec. above 150° C.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 20 hours
  3. temperaturecooled
  4. washwashed with ethyl acetate
  5. extractionextracted twice with ethyl acetate
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto afford a tan solid, 32 mg (32%), mp dec
  10. customabove 150° C.

Sources & evidence

ORD record
ord-8017869953c4410fb31dc80ed22461ff
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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