Hydrochloric Acid → 148296-18-8

HRID 2226380Notes

Reaction equation

HRID 2226380 reaction equation
C(N(CC)CC)C.Cl.[CH:9]12[O:16][CH:13]([CH2:14][CH2:15]1)[CH2:12][NH:11][CH2:10]2.[Cl:17][C:18]1[N:23]=[C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)[N:21]=[C:20]([CH3:28])[N:19]=1.Cl>O1CCOCC1.C(OCC)C>[ClH:17].[CH:25]1([NH:24][C:22]2[N:21]=[C:20]([CH3:28])[N:19]=[C:18]([N:11]3[CH2:10][CH:9]4[O:16][CH:13]([CH2:14][CH2:15]4)[CH2:12]3)[N:23]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 18965208148312-27-0HCID 219835368-Oxa-3-aza-bicyclo(3.2.1)octane hydrochloride

Product 1

HCID 3073354148296-18-8Yield 63%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

2 equivalents of triethylamine dissolved in dioxane are added to one equivalent of 8-oxa-3-azabicyclo[3,2,1]octane hydrochloride suspended in the same solvent. 1 equivalent of 2-chloro-4-cyclopropylamino-6-methyl-1,3,5-triazine dissolved in dioxane is then added. The mixture is heated under reflux for some hours. It is cooled to room temperature and the precipitate which has formed is filtered off. The filtrate is evaporated under reduced pressure and the residue is redissolved in dichloromethane. The solution is washed with water. The organic phase is separated off and dried over sodium sulfate, and the solvent is then evaporated under reduced pressure. The residue thus obtained is purified by chromatography on silica (eluent: 98:2 (v/v) dichloromethane-ethanol). 2-cyclopropylamino-4-methyl-6-(8-oxa-3-azabicyclo[3,2,1]oct-3-yl)-1,3,5-triazine hydrochloride is prepared by addition of one equivalent of hydrochloric acid to the free base in diethyl ether. Yield: 63%. M.P.: 220°-223° C.

Workup

  1. additionis then added
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for some hours
  4. customthe precipitate which has formed
  5. filtrationis filtered off
  6. customThe filtrate is evaporated under reduced pressure
  7. dissolutionthe residue is redissolved in dichloromethane
  8. washThe solution is washed with water
  9. customThe organic phase is separated off
  10. dry with materialdried over sodium sulfate
  11. customthe solvent is then evaporated under reduced pressure
  12. customThe residue thus obtained
  13. customis purified by chromatography on silica (eluent: 98:2 (v/v) dichloromethane-ethanol)

Sources & evidence

ORD record
ord-66db20cb4de54c60ad73bd4a917b6682
Source dataset
uspto-grants-1994_09
Patent number
US05348956

Reaction notes

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