Ammonium formate → HCID 58860672, compound

HRID 1350427Notes

Reaction equation

HRID 1350427 reaction equation
C([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:14][CH2:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[C:16]1([CH2:15][CH2:14][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58860596HCID 58860596, compound

Product 1

HCID 58860672HCID 58860672, compoundYield 367.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1-benzyl-2-(2-naphthalen-1-yl-ethyl)-piperazine (280 mg, 0.85 mmol) in ethanol (5 mL). Add ammonium formate (320 mg, 5.1 mmol) and palladium hydroxide (60 mg, 20 wt. % on carbon) and heat to reflux. After 5.5 h, filter the palladium hydroxide and concentrate the filtrate. Combine with Example 421 and purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (5%) and 7N ammonia in methanol-methylene chloride (20%) as the eluent to give 750 mg (81%) of the title compound: mass spectrum (ion spray): m/z=241 (M+1). 1H NMR (DMSO-d6): 8.08 (d, 1H), 7.91 (d, 1H), 7.76 (d, 1H), 7.59–7.32 (m, 4H), 3.53 (br s, 2H), 3.22–3.09 (m, 1H), 3.08–2.98 (m, 1H), 2.98–2.73 (m, 3H), 2.71–2.53 (m, 3H), 2.31 (dd, 1H), 1.71–1.57 (m, 2H).

Workup

  1. filtrationfilter the palladium hydroxide
  2. concentrationconcentrate the filtrate
  3. customCombine with Example 421 and purify by silica gel chromatography

Sources & evidence

ORD record
ord-c6fc756ff67042f39964d1cdcba40473
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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