Hydrochloric Acid → HCID 68523105, compound

HRID 655346Notes

Reaction equation

HRID 655346 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:16][CH:15]3[N:17](C)[CH:11]([CH2:12][CH2:13][CH2:14]3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].ClC(Cl)(Cl)COC(Cl)=O.[OH-].[Na+].Cl>C(OCC)C.[Zn].O.C(O)(=O)C.C1(C)C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:16][CH:15]3[NH:17][CH:11]([CH2:12][CH2:13][CH2:14]3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 24742885HCID 24742885, compound

Product 1

HCID 68523105HCID 68523105, compound

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-(3,4-dichloro-phenyl)-9-methyl-3,9-diaza-bicyclo[3.3.1]nonane (0.50 g, 1.75 mmol), 2,2,2-trichloroethylchloroformate (1.11 g, 5.26 mmol) and toluene (30 ml) was stirred at reflux for 15 h. Water (30 ml) was added and the phases were separated. The organic phase was evaporated. Acetic acid (10 ml) and water (10 ml) and zinc powder (0.57 g, 8.8 mmol) was added. The mixture was stirred for 15 h. Aqueous sodium hydroxide (20 ml, 1 M) was added followed by extraction with dichloromethane (3×10 ml). The crude product was purified by silica gel column chromatography using a solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%). Yield 150 mg (32%). The corresponding salt was obtained by addition a mixture of hydrogen chloride solved in diethylether (1 ml, 2 M). Mp 295.4° C. LC-ESI-HRMS of [M+H]+ shows 271.0769 Da. Calc. 271.076879 Da, dev. 0.1 ppm.

Workup

  1. temperatureat reflux for 15 h
  2. customthe phases were separated
  3. customThe organic phase was evaporated
  4. stirringThe mixture was stirred for 15 h
  5. extractionfollowed by extraction with dichloromethane (3×10 ml)
  6. customThe crude product was purified by silica gel column chromatography
  7. additiona solvent mixture of dichloromethane, methanol and aqueous ammonia (9:1:1%)
  8. customThe corresponding salt was obtained by addition

Sources & evidence

ORD record
ord-45572e4efe714f00b2ca0b6971fdd21d
Source dataset
uspto-grants-2011_12
Patent number
US08071598B2

Reaction notes

Loading…