Ethanol → HCID 12082741, compound

HRID 1977902Notes

Reaction equation

HRID 1977902 reaction equation
CC1NC(C)=CC=1C1C=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH2:20][N:21]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:22][CH2:23][CH:24]=3)=[CH:15][CH:14]=2)[N:8]=1.Cl.[NH2:34]O.[CH2:36](O)[CH3:37]>O>[CH2:25]([N:21]1[CH2:22][CH2:23][CH:24]=[C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:9]3[N:8]=[C:37]([NH2:34])[CH:36]=[CH:11][CH:10]=3)=[CH:18][CH:17]=2)[CH2:20]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 69869319HCID 69869319, compound

Product 1

HCID 12082741HCID 12082741, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 135 mg (0.322 mmol) 2-(2,5-dimethylpyrrolyl)-6-[4-(1-benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-phenyl]-pyridine, 112 mg (1.61 mmol) hydroxylamine hydrochloride, 5 mL ethanol, and 1 mL water. The reaction was refluxed 40 hours cooled, and the resulting precipitate, 6-[4-(1-benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-phenyl]-pyridin-2-ylamine dihydrochloride, filtered and dried, 22 mg (16.5%), mp 270-272° C. Additional material was recovered from the filtrate, 60 mg (55%) of the free base as an oil.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 40 hours
  3. temperaturecooled
  4. filtrationthe resulting precipitate, 6-[4-(1-benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-phenyl]-pyridin-2-ylamine dihydrochloride, filtered
  5. customdried
  6. customAdditional material was recovered from the filtrate, 60 mg (55%) of the free base as an oil

Sources & evidence

ORD record
ord-afcf125d2e7d42289e073af5571835a6
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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