Ammonium formate → HCID 18415743, compound

HRID 990747Notes

Reaction equation

HRID 990747 reaction equation
[ClH:1].C([N:9]1[CH2:20][CH:19]2[CH2:21][CH:11]([CH2:12][C:13]3[C:14]([O:22][CH3:23])=[CH:15][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].[CH3:23][O:22][C:14]1[C:13]2[CH2:12][CH:11]3[CH2:21][CH:19]([CH2:20][NH:9][CH2:10]3)[C:18]=2[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 18415740HCID 18415740, compound

Product 1

HCID 18415743HCID 18415743, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

11-Benzyl-6-methoxy-11-aza-tricyclo[7.3.1.02,7]trideca-2(7),3,5-triene hydrochloride (525 mg, 1.64 mmol), ammonium formate (2.07 g, 32.0 mmol and 10% palladium hydroxide on carbon (Pd(OH)2/C) (200 mg) were combined in MeOH (30 mL) and refluxed for 2 hours. The mixture was filtered hot through Celite and the filtrate concentrated then azeotroped from MeOH (5×50 mL) to yield a solid. This was recrystallized from MeOH/Et2O to provide a white solid (306 mg, 81%). 1H NMR (free base, CDCl3) δ7.15 (t, J=8.0 Hz, 1H), 6.74 (d, J=8.0 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 3.82 (s, 3H), 3.34 (br d, J=13.0 Hz, 1H), 3.11-3.02 (m, 4H), 2.94 (AB d, J=18.3 Hz, 1H), 2.87 (AB dd, J=18.3,6.5 Hz, 1H), 2.41 (br s, 1H), 1.91 (AB q, 2H). GSMS m/e 203 (M+). mp 272-274° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe mixture was filtered hot through Celite
  3. concentrationthe filtrate concentrated
  4. customthen azeotroped from MeOH (5×50 mL)
  5. customto yield a solid
  6. customThis was recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-5e301e72ca2f4ffebe6b3945b991e425
Source dataset
uspto-grants-2002_10
Patent number
US06462035B1

Reaction notes

Loading…