Ammonium formate → (S)-2-(2-Pyridin-2-yl-ethyl)-piperazine

HRID 1350363Notes

Reaction equation

HRID 1350363 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][CH:26]=[CH:25][N:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[N:24]1[CH:25]=[CH:26][CH:27]=[CH:28][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 17759583(S)-1,4-dibenzyl-2-(2-pyridinyl-ethyl)-piperazine

Product 1

HCID 17759584(S)-2-(2-Pyridin-2-yl-ethyl)-piperazineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-pyridin-2-yl-ethyl)-piperazine (2.86 g, 7.69 mmol) in ethanol (50 mL). Add ammonium formate (2.43 g, 38.5 mmol) and palladium (430 mg, 5 wt. % on carbon) and heat to reflux. After 6 hours 40 minutes, filter the palladium on carbon and concentrate the filtrate. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (5%–15%) as the eluent to give the title compound (1.1 g, 75%): mp 83–87° C.; mass spectrum (ion spray): m/z=192 (M+1). Analysis calculated for C11H17N3: C, 69.07; H, 8.96; N, 21.97. Found: C, 68.84; H, 8.85; N, 21.65.

Workup

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

Sources & evidence

ORD record
ord-3e9af1f654234f8ea366754c3babaa20
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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