HCID 54142805, compound → HCID 9882676, compound

HRID 963366Notes

Reaction equation

HRID 963366 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:18])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[C:4]([O:19][CH3:20])[CH:3]=1>C(O)(=O)C>[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](=[O:18])[CH2:10][CH2:11][CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[C:4]([O:19][CH3:20])[CH:3]=1

Participants

3

Reactant 1

HCID 54142805HCID 54142805, compound

Product 1

HCID 9882676HCID 9882676, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(4-Amino-5-chloro-2-methoxyphenyl)-3-(pyridin-4-yl)-2-propen-1-one (0.5 g, 1.7 mmol), prepared as in Example 6, Step (b), was dissolved in acetic acid (25 mL) and the solution was hydrogenated over 5% rhodium-alumina catalyst (0.2 g) at 50 psi for 24 hours. The solution was filtered, diluted with water, basified with ammonium hydroxide, and extracted three times with methylene chloride. The combined extracts were dried over sodium sulfate. Evaporation gave 1-(4-amino-5-chloro-2-methoxyphenyl)-3-(piperidin-4-yl)propan-1-one (0.35 g, 1.2 mmol).

Workup

  1. filtrationThe solution was filtered
  2. additiondiluted with water
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customEvaporation

Sources & evidence

ORD record
ord-dfd2af3ae49845738e33fee652c71270
Source dataset
uspto-grants-1998_06
Patent number
US05763458

Reaction notes

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