HCID 22662746, compound → [1-(2-Amino-ethyl)-4-piperidinyl]methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylate

HRID 392067Notes

Reaction equation

HRID 392067 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][C:23]#[N:24])[CH2:18][CH2:17]2)=[O:13])=[CH:4][C:3]=1[Cl:25].[H][H]>C1COCC1.[Ni]>[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([O:14][CH2:15][CH:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][NH2:24])[CH2:18][CH2:17]2)=[O:13])=[CH:4][C:3]=1[Cl:25]

Participants

5

Reactant 2

HCID 22662746HCID 22662746, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22662752[1-(2-Amino-ethyl)-4-piperidinyl]methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylateYield 68%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate 14 (6 g) in THF (250 ml) was hydrogenated with Raney nickel (3 g) as a catalyst. After uptake of hydrogen (2 equivalents), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent CH2Cl2/(CH3OH/NH3) 90/10). The pure fractions were collected and the solvent was evaporated, yielding 4 g (68%) [1-(2-amino-ethyl)-4-piperidinyl]methyl 8-amino-7-chloro-2,3-dihydro-1,4-benzodioxin-5-carboxylate (intermediate 15).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was purified by column chromatography over silica gel (eluent CH2Cl2/(CH3OH/NH3) 90/10)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-017ebf544c2543a0a323ca1e02abda66
Source dataset
uspto-grants-2004_10
Patent number
US06800628B2

Reaction notes

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