Acrylonitrile → [1-(2-Cyanoethyl)-4-piperidinyl]methyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate

HRID 53636Notes

Reaction equation

HRID 53636 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:23](#[N:26])[CH:24]=[CH2:25]>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]([CH2:25][CH2:24][C:23]#[N:26])[CH2:20][CH2:21]2)=[O:13])=[CH:4][C:3]=1[Cl:22]

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 190681434-Piperidinylmethyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate

Product 1

HCID 19068140[1-(2-Cyanoethyl)-4-piperidinyl]methyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylateYield 17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Piperidinylmethyl 8-amino-7-chloro-1,4-benzodioxan-5-carboxylate (0.180 g, 0.55 mmol) was dissolved in acetone (10 ml) and treated with acrylonitrile (0.040 ml; 0.61 mmol). The solution was heated at reflux (18 hours), cooled and evaporated in vacuo to an orange gum. The gum was purified by flash silica-gel chromatography with CHCl3 →2% MeOH/CHCl3 as eluant to yield the title compound as a colourless oil (0.035g; 17%) which was converted to the oxalate salt, mp 101°-103° C.

Workup

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

Sources & evidence

ORD record
ord-1a5d1df502644fe0aa7eae71012692c2
Source dataset
uspto-grants-1997_04
Patent number
US05620992

Reaction notes

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