Ammonium formate → HCID 20634913, compound

HRID 49167Notes

Reaction equation

HRID 49167 reaction equation
[ClH:1].C([N:9]1[CH2:20][CH:19]2[CH2:21][CH:11]([CH2:12][C:13]3[CH:14]=[C:15]([CH2:22][CH3:23])[CH:16]=[CH:17][C:18]=32)[CH2:10]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[ClH:1].[CH2:22]([C:15]1[CH:16]=[CH:17][C:18]2[CH:19]3[CH2:21][CH:11]([CH2:12][C:13]=2[CH:14]=1)[CH2:10][NH:9][CH2:20]3)[CH3:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 20634909HCID 20634909, compound

Product 1

HCID 20634913HCID 20634913, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

11-Benzyl-5-Ethyl-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (160 mg, mmol), ammonium formate (220 mg, 3.49 mmol) and 10% Pd(OH)2/C (100 mg) were combined in methanol (MeOH) (5 mL) and warmed to reflux for 15 min. The mixture was cooled, filtered, concentrated, diluted with sat. aq. Na2CO2 soln. and extracted with EtOAc (3×20 mL). The extracts were dried (MgSO4), filtered and concentrated to an oil (94 mg, 83%). (TLC 50% EtOAc/hexanes (NH3) Rf 0.20). 1H NMR (CDCl3) δ 6.90 (d, J=9.0 Hz, 1H). 6.66 (2H), 3.97 (m, 2H), 3.08 (dd, J=18.0, 6.0 Hz, 1H), 2.94 (m, 3H), 2.76-2.65 (3H), 1.96 (m, 2H), 1.88 (d, J=11.0 Hz, 1H), 1.38 (t, J=7.0 Hz, 3H). This material was dissolved in excess 1N HCl MeOH and concentrated. Recrystallization from CH2Cl2/Et2O provided a solid (74 mg, 68%). mp 243-245° C.

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 15 min
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additiondiluted with sat. aq. Na2CO2 soln
  7. extractionand extracted with EtOAc (3×20 mL)
  8. dry with materialThe extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated to an oil (94 mg, 83%)
  11. dissolutionThis material was dissolved in excess 1N HCl MeOH
  12. concentrationconcentrated
  13. customRecrystallization from CH2Cl2/Et2O

Sources & evidence

ORD record
ord-581abb0b664f434fa1048cd2112a806d
Source dataset
uspto-grants-2004_03
Patent number
US06706702B2

Reaction notes

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