Ammonium formate → HCID 45115805, compound

HRID 1350377Notes

Reaction equation

HRID 1350377 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:24]=[N:25][CH:26]=[CH:27][CH:28]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[N:25]1[CH:26]=[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:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 69486878HCID 69486878, compound

Product 1

HCID 45115805HCID 45115805, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-pyridin-3-yl-ethyl)-piperazine (1.6 g, 4.31 mmol) in ethanol (30 mL). Add ammonium formate (1.63 g, 25.8 mmol) and palladium (240 mg, 5 wt. % on carbon) and heat to reflux. After 3 hours 30 minutes, add additional ammonium formate (1.63 g, 25.8 mmol). After 3 hours, filter the palladium on carbon and concentrate the filtrate. Slurry the residue in water and methylene chloride, basify with 5N NaOH, and extract with methylene chloride and chloroform-isopropanol (3:1 mixture). Dry the extracts over sodium sulfate, filter and concentrate the filtrate. Purify by silica gel chromatography using 7N ammonia in methanol-methylene chloride (2.5%–15%) as the eluent to give (261 mg, 32%) of the title compound: mp 104–110° C.; mass spectrum (ion spray): m/z=192 (M+1). 1H NMR (DMSO-d6, D2O): δ8.42 (d, 1H), 8.38 (dd, 1H), 7.63 (dt, 1H), 7.31 (dd, 1H), 2.38–2.83 (m, 8H), 2.18 (dd, 1H), 1.50 (dd, 2H).

Workup

  1. waitAfter 3 hours
  2. filtrationfilter the palladium on carbon
  3. concentrationconcentrate the filtrate
  4. extractionextract with methylene chloride and chloroform-isopropanol (3:1 mixture)
  5. dry with materialDry the extracts over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate the filtrate
  8. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-07bd31d7ebe94065ba6627e6571186cb
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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