Ammonium formate → HCID 45099758, compound

HRID 1350435Notes

Reaction equation

HRID 1350435 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[CH:27]=[CH:26][O:25][CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[O:25]1[CH:26]=[CH:27][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:24]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58860637HCID 58860637, compound

Product 1

HCID 45099758HCID 45099758, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-furan-3-yl-ethyl)-piperazine (810 mg, 2.25 mmol) in ethanol (5 mL). Add ammonium formate (850 mg, 13.5 mmol) and palladium (100 mg, 5 wt. % on carbon) and heat to reflux. After 3.5 h, filter the palladium and concentrate the filtrate. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (5%) as the eluent to give 175 mg (43%) of the title compound: mass spectrum (ion spray): m/z=181 (M+1). Analysis calculated for C10H16N2O: C, 66.63; H, 8.95; N, 11.54. Found: C, 66.53; H, 8.92; N, 11.14.

Workup

  1. filtrationfilter the palladium
  2. concentrationconcentrate the filtrate
  3. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-68cf44fb422544ffaeb299146593a115
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…