Ethanol → (S)-2-(2-Pyridin-4-yl-ethyl)-piperazine

HRID 1350364Notes

Reaction equation

HRID 1350364 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=CN=1)C1C=CC=CC=1.C([O-])=O.[NH4+:32].[CH2:33](O)[CH3:34]>[Pd]>[N:32]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 17759583(S)-1,4-dibenzyl-2-(2-pyridinyl-ethyl)-piperazine

Product 1

HCID 45115809(S)-2-(2-Pyridin-4-yl-ethyl)-piperazineYield 86%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-pyridinyl-ethyl)-piperazine (2.14 g, 5.76 mmol) in ethanol (40 mL). Add ammonium formate (2.18 g, 34.6 mmol) and palladium (430 mg, 5 wt. % on carbon) and heat to reflux. After 6 hours 30 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 945 mg (86%) of the title compound: mp 113–116° 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, 69.08; H, 8.77; N, 21.81.

Workup

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

Sources & evidence

ORD record
ord-9278b8cc5ea34029aa6890f4327ea54c
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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