Hydrochloric Acid → HCID 178497572, compound

HRID 1348496Notes

Reaction equation

HRID 1348496 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([CH:22]=O)[CH2:18][CH2:17]1)(=[O:15])[CH3:14].Cl.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>CO.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:13]([N:16]1[CH2:21][CH2:20][CH:19]([C:22]2[NH:1][C:2]3[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[CH:10][C:11]=3[N:12]=2)[CH2:18][CH2:17]1)(=[O:15])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 73972Sodium sulfide nonahydrateHCID 5718252,3-Diaminobenzoic acid methyl esterHCID 184280371-Acetylpiperidine-4-carbaldehyde

Product 1

HCID 178497572HCID 178497572, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent3×

Procedure

3.3 g (19.9 mmol) of methyl 2,3-diaminobenzoate were dissolved in 100 ml of methanol, and a solution of 4.0 g (25.8 mmol) of N-acetylpiperidine-4-carbaldehyde in 100 ml of methanol was added dropwise at room temperature. The whole was stirred for about 10 minutes at room temperature. Thereafter, 5.2 g (25.8 mmol) of copper(II) acetate, which was dissolved in 100 ml of water, were added dropwise and the whole was refluxed for 30 minutes. After cooling, 25 ml of concentrated hydrochloricacid were added carefully and the whole was again refluxed. 7.15 g (29.8 mmol) of sodium sulfide nonahydrate, dissolved in 100 ml of water, were then added dropwise and the whole was boiled for a further 10 minutes. After cooling, the reaction solution was evaporated down under reduced pressure. The residue obtained was dispersed in water and filtered. The filtrate was rendered alkaline with aqueous sodium bicarbonate solution and was extracted several times with ethyl acetate. The combined organic phases were washed with water, dried and evaporated down under reduced pressure. 4.5 g of the product were obtained.

Workup

  1. additionwere added dropwise
  2. temperaturethe whole was refluxed for 30 minutes
  3. temperatureAfter cooling
  4. temperaturethe whole was again refluxed
  5. additionwere then added dropwise
  6. waitthe whole was boiled for a further 10 minutes
  7. temperatureAfter cooling
  8. customthe reaction solution was evaporated down under reduced pressure
  9. customThe residue obtained
  10. filtrationfiltered
  11. extractionwas extracted several times with ethyl acetate
  12. washThe combined organic phases were washed with water
  13. customdried
  14. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-d69a937f6d0e49b38ff15c3011adfcc1
Source dataset
uspto-grants-2007_05
Patent number
USRE039608E1

Reaction notes

Loading…