Ammonium formate → HCID 58860672, compound

HRID 1350425Notes

Reaction equation

HRID 1350425 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:23]1([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.[CH2:14]([N:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:21][CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)[CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 2723923Ammonium formateHCID 58860627HCID 58860627, compound

Product 3

HCID 58860596HCID 58860596, compoundHCID 58860650HCID 58860650, compoundHCID 58860672HCID 58860672, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve (S)-1,4-dibenzyl-2-(2-naphthalen-1-yl-ethyl)-piperazine (3.33 g, 7.92 mmol) in ethanol (100 mL). Add ammonium formate (2.99 g, 47.5 mmol) and palladium (666 mg, 5 wt. % on carbon) and heat to reflux. After 6 h 30 min, filter the palladium on carbon and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (2.5%–10%) and 7N ammonia in methanol-methylene chloride (20%) as the eluent to give 716 mg (38%) of (S)-2-(2-naphthalen-1-yl-ethyl)-piperazine, 1.1 g of (S)-1-benzyl-3-(2-naphthalen-1-yl-ethyl)-piperazine, and 290 mg of (S)-1-benzyl-2-(2-naphthalen-1-yl-ethyl)-piperazine.

Workup

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

Sources & evidence

ORD record
ord-1a2e26077a344ab9a4a2ebbf5a51c7cc
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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