Hydrochloric Acid → HCID 18766246, compound

HRID 858173Notes

Reaction equation

HRID 858173 reaction equation
O1CCCCC1[O:7][CH:8]([CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[CH2:9][O:10][N:11]=[C:12]([Cl:19])[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[CH2:27]([NH2:31])[CH2:28][CH2:29][CH3:30].Cl>C(O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(C)C>[ClH:19].[OH:7][CH:8]([CH2:20][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:9][O:10][NH:11][C:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[N:31][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8007ButylamineHCID 54390744HCID 54390744, compound

Product 1

HCID 18766246HCID 18766246, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 3776IsopropanolSolventHCID 6101p-Toluenesulfonic acidSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3.7 g (9.68 mmol) of N-[2-[(2-tetrahydropyranyl)oxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride and 40 ml (0.41 mol) n-butylamine was refluxed for 3 hours. The excess of amine was evaporated in vacuum affording dark-brown oil, which was dissolved in 40 ml of ethanol containing 3.0 g of 4-toluenesulphonic acid and the mixture was heated at 60° C. for one hour. The solvent was removed under reduced pressure, the residue was made alkaline (pH 10) with 2 N of sodium hydroxide solution then extracted three times with chloroform. The organic solution was dried over sodium sulfate, filtered and the solvent was evaporated in vacuum. The dark oily residue was purified by chromatography to give the pure base, which was dissolved in 20 ml of ethanol and acidified with equivalent amount of dry hydrochloric acid dissolved in isopropyl alcohol to give the title compound as a pale-yellow crystalline solid.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe excess of amine was evaporated in vacuum
  3. customaffording dark-brown oil, which
  4. customThe solvent was removed under reduced pressure
  5. extractionthen extracted three times with chloroform
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated in vacuum
  9. customThe dark oily residue was purified by chromatography
  10. customto give the pure base, which

Sources & evidence

ORD record
ord-e723688e22f44f85ab3c1e267319fdd5
Source dataset
uspto-grants-2006_12
Patent number
US07148239B2

Reaction notes

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