Ammonium formate → HCID 58860736, compound

HRID 1350431Notes

Reaction equation

HRID 1350431 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:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[CH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:31]=[CH:32][C:23]=1[CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58860700HCID 58860700, compound

Product 1

HCID 58860736HCID 58860736, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-naphthalen-2-yl-ethyl)-piperazine (6.53 g, 15.5 mmol) in ethanol (80 mL). Add ammonium formate (5.9 g, 93.6 mmol) and palladium hydroxide (1.5 g, 20 wt. % on carbon) and heat to reflux. After 8.5 h, cool and stir at ambient temperature 18 h. Filter the palladium hydroxide and concentrate the filtrate. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (2.5%–10%) as the eluent to give 2.86 g (77%) of the title compound: mp 151–4° C.; mass spectrum (ion spray): m/z=241 (M+1).

Workup

  1. temperaturecool
  2. filtrationFilter the palladium hydroxide
  3. concentrationconcentrate the filtrate
  4. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-a567d366aa1441ce864b054e27a9e665
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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