Valeryl chloride → HCID 86733654, compound

HRID 1659204Notes

Reaction equation

HRID 1659204 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:16]=3[CH:15]3[CH:10]([CH2:11][CH2:12][N:13]([CH3:26])[CH2:14]3)[N:9]=2)=[CH:4][CH:3]=1.[C:27](Cl)(=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31]>C(#N)C>[CH3:25][O:24][C:19]1[C:20]([O:22][CH3:23])=[CH:21][C:16]2[C@H:15]3[C@H:10]([CH2:11][CH2:12][N:13]([CH3:26])[CH2:14]3)[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:27](=[O:32])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:3][CH:4]=3)[C:17]=2[CH:18]=1

Participants

4

Reactant 2

HCID 61186Valeryl chlorideHCID 18966392HCID 18966392, compound

Product 1

HCID 86733654HCID 86733654, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3 g of 6-(4-aminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydro-benzo[c][1,6]naphthyridine and 6,2 g of valeric acid chloride are heated to the boil under reflux in 70 ml of acetonitrile for 7 hours. The reaction mixture is evaporated to dryness in a vacuum, water is added to the residue, the reaction mixture is made alkaline with potassium carbonate and extracted with methylene chloride. The solution is concentrated by evaporation, the crude product is dissolved in ethanol and a slight excess of hydrochloric acid in ethanol is added, whereby the title compound crystallizes in dihydrochloride form (melting point: 230°-235°).

Workup

  1. customThe reaction mixture is evaporated to dryness in a vacuum, water
  2. additionis added to the residue
  3. extractionextracted with methylene chloride
  4. concentrationThe solution is concentrated by evaporation
  5. dissolutionthe crude product is dissolved in ethanol
  6. additiona slight excess of hydrochloric acid in ethanol is added
  7. customwhereby the title compound crystallizes in dihydrochloride form (melting point: 230°-235°)

Sources & evidence

ORD record
ord-953e5b68b68e46e585b20ea7c4078b95
Source dataset
uspto-grants-1976_06
Patent number
US03966938

Reaction notes

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