Hydrochloric Acid → HCID 12082745, compound

HRID 1977905Notes

Reaction equation

HRID 1977905 reaction equation
CC1NC(C)=CC=1C1C=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][N:21]3[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:15][CH:14]=2)[N:8]=1.Cl.[NH2:35]O.[CH2:37](O)[CH3:38].Cl>O>[CH2:26]([N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH:20]1[CH2:19][C:16]1[CH:15]=[CH:14][C:13]([C:9]2[N:8]=[C:38]([NH2:35])[CH:37]=[CH:11][CH:10]=2)=[CH:18][CH:17]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 443297Hydroxyamine hydrochloride2×HCID 54447250HCID 54447250, compound

Product 1

HCID 12082745HCID 12082745, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 36 mg (0.0827 mmol) 2-(2,5-dimethylpyrrolyl)-6-[4-(1-benzyl-piperidin-2-ylmethyl)-phenyl]-pyridine, 29 mg (0.414 mmol) hydroxylamine hydrochloride, 4 mL ethanol and 1 mL water. The reaction was refluxed 84 h (additional hydroxylamine hydrochloride was used to complete the reaction), cooled, poured into dilute hydrochloric acid, and washed with ethyl acetate. The aqueous layer was adjusted to pH 10 with 6 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 converted to the hydrochloride salt using 1 N HCl in ether to afford a solid, 17 mg (48%), mp 70-85° C.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. customthe reaction),
  3. temperaturecooled
  4. washwashed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customto afford a solid, 17 mg (48%), mp 70-85° C.

Sources & evidence

ORD record
ord-d1a0730434844d29b653cad7b200d378
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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