Ammonium formate → HCID 21093530, compound

HRID 1350385Notes

Reaction equation

HRID 1350385 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:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69486828(s)-1,4-Dibenzyl-2-(2-(4-methoxy-phenyl)-ethyl)-piperazine

Product 1

HCID 21093530HCID 21093530, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(4-methoxy-phenyl)-ethyl)-piperazine (1.34 g, 3.33 mmol), ammonium formate (1.05 g, 16.67 mmol), 5% Pd/C (161.2 mg), and ethanol (100 mL). Stir and heat the mixture at reflux. After 3 hours, cool to ambient temperature and remove the catalyst by vacuum filtration through celite. Reduce the filtrate to residue and purify it on silica gel using dichloromethane/2N ammonia in methanol (80:20) to give (689.3 mg, 94%) of the title compound as a white solid: mp 125–130° C.; mass spectrum (ion spray): m/z=221.1 (M+1); Analysis for C13H20N2O: calcd: C, 70.87; H, 9.15; N, 12.72; found: C, 70.58; H, 9.05; N, 12.61.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. customremove the catalyst
  4. filtrationby vacuum filtration through celite
  5. custompurify it on silica gel

Sources & evidence

ORD record
ord-04cde20aecb942ea8928280f463ff9fc
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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