Hydrochloric Acid → HCID 19773289, compound

HRID 1614270Notes

Reaction equation

HRID 1614270 reaction equation
[ClH:1].C([N:5]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:14]2)[CH2:6][C:7]#[CH:8])(=O)C.Cl>C(O)C>[ClH:1].[ClH:1].[CH2:6]([NH:5][C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH:13]([NH:19][CH2:20][CH2:21][CH3:22])[CH2:14]2)[C:7]#[CH:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19773344HCID 19773344, compound

Product 1

HCID 19773289HCID 19773289, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.48 g (0.0015 mol) of 5-(N-acetyl-N-propargyl-amino)-2-n-propylamino-tetraline-hydrochloride (Example 4.7.11) are refluxed in 10 ml of ethanol and 30 ml of 6 N hydrochloric acid for 16 hours. The mixture is then concentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum. The residue is shaken with 50 ml of water, 50 ml of methylene chloride and excess ammonia. The aqueous phase separated off is extracted twice more with 15 ml of methylene chloride. The combined methylene chloride extracts are washed with 20 ml of water and concentrated by rotary evaporation as described above. The residue is crystallised analogously to Example 4.1.1 in the form of the dihydrochloride. Yield 0.12 g (25.2% of theory), melting point 198° C., unchanged after recrystallisation from ethanol/ether.

Workup

  1. concentrationThe mixture is then concentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum
  2. customThe aqueous phase separated off
  3. extractionis extracted twice more with 15 ml of methylene chloride
  4. washThe combined methylene chloride extracts are washed with 20 ml of water
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue is crystallised analogously to Example 4.1.1 in the form of the dihydrochloride
  7. customYield 0.12 g (25.2% of theory), melting point 198° C., unchanged after recrystallisation from ethanol/ether

Sources & evidence

ORD record
ord-d486e7a2c7574cb8a026af3353029fa7
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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