Methyl vinyl ketone → [1-(3-Oxobutyl)-4-piperidinyl]methyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate

HRID 53637Notes

Reaction equation

HRID 53637 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][NH:19][CH2:18][CH2:17]2)=[O:13])=[CH:4][C:3]=1[Cl:22].C(N(CC)CC)C.[CH:30]([C:32]([CH3:34])=[O:33])=[CH2:31]>CC(C)=O>[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[CH2:17][CH2:18][N:19]([CH2:31][CH2:30][C:32](=[O:33])[CH3:34])[CH2:20][CH2:21]2)=[O:13])=[CH:4][C:3]=1[Cl:22]

Participants

5

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 190681434-Piperidinylmethyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate

Product 1

HCID 19068145[1-(3-Oxobutyl)-4-piperidinyl]methyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Piperidinylmethyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate (0.100 g; 10.31 mmol) was dissolved in acetone (10 ml) and treated with triethylamine (0.043 ml; 0.31 mmol) and methyl vinyl ketone (0.026 ml; 0.34 mmol). The solution was heated at reflux (18 hours), cooled and evaporated in vacuo to a yellow gum. The gum was purified by flash silica-gel chromatography with CHCl3 as eluant to yield the title compound as a colourless gum (0.050 g; 41%) which was converted to the oxalate salt.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux (18 hours)
  3. temperaturecooled
  4. customevaporated in vacuo to a yellow gum
  5. customThe gum was purified by flash silica-gel chromatography with CHCl3 as eluant

Sources & evidence

ORD record
ord-46ed0bfdf9c946048908994b9e57316c
Source dataset
uspto-grants-1997_04
Patent number
US05620992

Reaction notes

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