Triethylamine → 2-([2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]piperid-4-yl)-1H-isoindole-1,3-(2H)-dione

HRID 66559Notes

Reaction equation

HRID 66559 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12]Br.Cl.[NH:16]1[CH2:21][CH2:20][CH:19]([N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH:11]([OH:14])[CH2:12][N:16]1[CH2:21][CH2:20][CH:19]([N:22]2[C:23](=[O:32])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]2=[O:31])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olHCID 218825602-(Piperidin-4-yl)isoindoline-1,3-dione hydrochloride

Product 1

HCID 130189842-([2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]piperid-4-yl)-1H-isoindole-1,3-(2H)-dione

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Erythro, 1-(1,4-benzodioxan-2-yl)-2-bromoethanol (1.29 g, 0.005 m) and 2-(piperid-4-yl)-1H-isoindole-1,3-(2H)dione hydrochloride (1.33 g, 0.005 cm3) in ethanol (75 cm3) with triethylamine (3.03 g, 0.03 cm3) were refluxed for 18 hours. The solution was cooled and the solvent evaporated. the residue was dissolved in chloroform and then washed twice with water, dried (MgSO4) and evaporated. The residue was dissolved in isopropyl alcohol and acidified with ethanolic HCl. The crystallised material was filtered to give the title compound as the hydrochloride salt m.p. 235°-237° C.

Workup

  1. temperatureThe solution was cooled
  2. customthe solvent evaporated
  3. dissolutionthe residue was dissolved in chloroform
  4. washwashed twice with water
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in isopropyl alcohol
  8. filtrationThe crystallised material was filtered

Sources & evidence

ORD record
ord-b3907f74c53142b48cdc5f4b528aef75
Source dataset
uspto-grants-1982_08
Patent number
US04342761

Reaction notes

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