Ammonia → HCID 68523105, compound

HRID 643277Notes

Reaction equation

HRID 643277 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+].N.Cl>C(OCC)C.[Zn].CO.ClCCl.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

13

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 24742885HCID 24742885, compound

Product 1

HCID 68523105HCID 68523105, compound

Reagents, catalysts & solvents 7

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

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 get 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
  7. customget column chromatography
  8. customThe corresponding salt was obtained by addition

Sources & evidence

ORD record
ord-b6a3dd83a24244abbda557de4fb15014
Source dataset
uspto-grants-2010_04
Patent number
US07700596B2

Reaction notes

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