Maleic Acid → 8-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one maleate

HRID 1389481Notes

Reaction equation

HRID 1389481 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:24])[CH2:12][N:13]1[CH2:23][CH2:22][C:16]2([O:20][C:19](=[O:21])[NH:18][CH2:17]2)[CH2:15][CH2:14]1.[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29]>C(OCC)C.C(O)C>[C:25]([OH:32])(=[O:31])/[CH:26]=[CH:27]\[C:28]([OH:30])=[O:29].[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:24])[CH2:12][N:13]1[CH2:23][CH2:22][C:16]2([O:20][C:19](=[O:21])[NH:18][CH2:17]2)[CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 444266Maleic AcidHCID 130166581-Oxa-3,8-diazaspiro[4.5]decan-2-one, 8-[2-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-hydroxyethyl]-

Product 1

HCID 705718378-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one maleate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

1.0 g of 8-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one is dissolved in a solution of 5 ml of diethyl ether and 5 ml of ethanol at 20°. To this solution is added 10 ml of a saturated solution of maleic acid in ethyl ether. The mixture is allowed to stand for one hour at room temperature. The resulting precipitate is recovered by filtration, washed three times with diethyl ether and then crystallized from a mixture to diethyl ether and ethanol affording 8-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one maleate.

Workup

  1. filtrationThe resulting precipitate is recovered by filtration
  2. washwashed three times with diethyl ether
  3. customcrystallized from a mixture to diethyl ether and ethanol

Sources & evidence

ORD record
ord-a5d14c596a7345cfb74c462d957fcbf2
Source dataset
uspto-grants-1981_01
Patent number
US04244961

Reaction notes

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