Ammonium formate → 4-(5-Fluoro-2,3-dihydro-benzofuran-7-yl)-piperazine

HRID 992044Notes

Reaction equation

HRID 992044 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:22]3[O:21][CH2:20][CH2:19][C:18]=3[CH:17]=[C:16]([F:23])[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:23][C:16]1[CH:15]=[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:22]2[O:21][CH2:20][CH2:19][C:18]=2[CH:17]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 184141301-Benzyl-4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-piperazine

Product 1

HCID 184141144-(5-Fluoro-2,3-dihydro-benzofuran-7-yl)-piperazineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-benzyl-4-(5-fluoro-2,3-dihydro-benzofuran-7-yl)-piperazine (2.06 g, 6.6 mmol), 10% palladium on carbon (0.6 g) and ammonium formate (0.83 g, 13 mmol) in ethanol (20 ml) was allowed to refux for 2 hours. The catalyst was filtered off and the solvent removed under vacuum. Chromatography (10-30% methanol-methylene chloride plus ammonium hydroxide) afforded 1.10 g (75%) of product as a yellow oil; MS EI m/e 222 (M)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8f1110fab6d94e9fbab18bee2f67ec22
Source dataset
uspto-grants-2002_10
Patent number
US06465482B2

Reaction notes

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