Hydrochloric Acid → HCID 70549035, compound

HRID 1680182Notes

Reaction equation

HRID 1680182 reaction equation
[C:1]12([NH:12][C:13](=[O:26])[CH2:14][N:15]3C(=O)C4=CC=CC=C4C3=O)[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1.O.NN.C(O)C.[ClH:33]>C1C=CC=CC=1>[ClH:33].[C:1]12([NH:12][C:13](=[O:26])[CH2:14][NH2:15])[CH2:10][CH:6]([CH2:7][CH2:8][CH2:9]1)[CH:5]1[CH2:11][CH:2]2[CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 54401911HCID 54401911, compound

Product 1

HCID 70549035HCID 70549035, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1.39 g (3.94 millimoles) of N-(1-tricyclo[4.3.1.12,5 ]undecyl)-2-phthalimidoacetamide, 0.30 g (4.37 millimoles) of 80% hydrazine hydrate and 10 ml of ethanol was refluxed under agitation for 4 hours. The reaction temperature was lowered to 60° C., and 5 ml of 10% hydrochloric acid was added and the mixture was agitated for 2 hours. After cooling, the precipitate was recovered by filtration, and the pH of the filtrate was adjusted to 9 with a 5% aqueous solution of sodium hydroxide and the mixture was extracted with diethyl ether. The diethyl ether solution was condensed, and the residue was dissolved in 20 ml of dry benzene and dry hydrogen chloride gas was blown into the solution. The formed white precipitate was recovered by filtration and recrystallized from ethanolacetone to obtain 0.59 g (the yield being 58%) of the intended compound having a melting point of 225° to 229° C.

Workup

  1. temperaturewas refluxed under agitation for 4 hours
  2. customwas lowered to 60° C.
  3. temperatureAfter cooling
  4. filtrationthe precipitate was recovered by filtration
  5. extractionthe mixture was extracted with diethyl ether
  6. customcondensed
  7. filtrationThe formed white precipitate was recovered by filtration
  8. customrecrystallized from ethanolacetone
  9. customto obtain 0.59 g (the yield

Sources & evidence

ORD record
ord-1b2920c4266046638fb931d6ce6ac9c3
Source dataset
uspto-grants-1981_06
Patent number
US04272536

Reaction notes

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