Acetic Acid → HCID 20304652, compound

HRID 1764257Notes

Reaction equation

HRID 1764257 reaction equation
C(O)(=O)C.[N:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][CH2:10][CH2:9][CH2:8]1)=O.O.Cl.[NH:20]1[CH2:25][CH2:24][C:23](=O)[CH2:22][CH2:21]1>[Zn].C(O)C>[NH:20]1[CH2:25][CH2:24][C:23](=[N:5][N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][CH2:10][CH2:9][CH2:8]2)[CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 2723901PiperonylamineHCID 12233800HCID 12233800, compound

Product 1

HCID 20304652HCID 20304652, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Glacial acetic acid (700 ml) is added dropwise to a vigorously stirred mixture of 62 g of 2,3,4,5-tetrahydro-5-nitroso-1,5-benzothiazepine, 49 g of 4-piperidone hydrochloride monohydrate, 400 ml of anhydrous ethanol, and 140 g of zinc dust, cooled in an ice-bath. After the addition is complete, the mixture is stirred at room temperature for 1 hr. and filtered. The residue is washed with a small quantity of ethanol and the combined filtrates heated at 65°-70° C for 1 hour and then stripped of ethanol and acetic acid under reduced pressure. The residual viscous liquid is dissolved in minimum quantity of water and added with stirring, to excess of well-cooled 25% aqueous sodium hydroxide. The mixture is thoroughly extracted with chloroform and the combined chloroform extracts washed well with water, dried over anhydrous magnesium sulfate and stripped of the solvent under reduced pressure. The residue on trituration with ether and cooling yields 2,3,4,5-tetrahydro-5-[(4-piperidylidene)amino]-1,5-benzothiazepine as cream colored crystals, m.p. 113-115°. A sample of this hydrazone melts at 115°-117° C. after recrystallization from a mixture of benzene and hexane.

Workup

  1. temperaturecooled in an ice-bath
  2. additionAfter the addition
  3. filtrationand filtered
  4. washThe residue is washed with a small quantity of ethanol
  5. temperaturethe combined filtrates heated at 65°-70° C for 1 hour
  6. dissolutionThe residual viscous liquid is dissolved in minimum quantity of water
  7. additionadded
  8. stirringwith stirring
  9. extractionThe mixture is thoroughly extracted with chloroform
  10. washthe combined chloroform extracts washed well with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. temperatureThe residue on trituration with ether and cooling

Sources & evidence

ORD record
ord-eb44b2ec8d6d404da89b0bb32917f95e
Source dataset
uspto-grants-1978_09
Patent number
US04115577

Reaction notes

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