Hydrochloric Acid → HCID 13423339, compound

HRID 1248578Notes

Reaction equation

HRID 1248578 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([C:13](Cl)=[O:14])[CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1.[N:23]1([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.Cl>C1C=CC=CC=1>[N:23]1([CH2:29][CH2:30][CH2:31][NH:32][C:13]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[O:4][C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=2)=[C:2]([CH3:1])[C:11]3=[O:12])=[O:14])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19049Piperidine-1-propylamineHCID 54140054HCID 54140054, compound

Product 1

HCID 13423339HCID 13423339, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3,3'-dimethylflavone-8-carboxylic acid chloride (prepared from 1.00 g of 3,3'-dimethylflavone-8-carboxylic acid and 0.50 ml of thionyl chloride) in 30 ml of benzene were added 0.44 g of 3-piperidinopropylamine and the mixture was stirred for 2 hours at room temperature. To the mixture was added aqueous HCl soluction and the mixture was shaken. The water layer was separated and made alkaline with potassium carbonate and extracted with chloroform. The extract was washed with water, dried, and evaporated, and to the residue was added isopropyl ether. The precipitate was filtered to give 0.80 g of reddish brown crystals, which were recrystallized from a mixture of acetone and water as colorless needles, m.p. 112°-114° C.

Workup

  1. stirringthe mixture was shaken
  2. customThe water layer was separated
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated
  7. additionto the residue was added isopropyl ether
  8. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-479eddaf488a476d96adb3c683b12879
Source dataset
uspto-grants-1985_06
Patent number
US04525356

Reaction notes

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