1,4,10-Trioxa-7,13-diazacyclopentadecane-8,12-dione → 1,4,10-Trioxa-7,13-diazacyclopentadecane

HRID 1658912Notes

Reaction equation

HRID 1658912 reaction equation
O=[C:2]1[CH2:16][O:15][CH2:14][C:13](=O)[NH:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[O:6]1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][O:15][CH2:16][CH2:2][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 126780651,4,10-Trioxa-7,13-diazacyclopentadecane-8,12-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 1234351,4,10-Trioxa-7,13-diazacyclopentadecaneYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 15.7 g. of the diamide obtained in Example 40 in 300 ml. hot anhydrous tetrahydrofuran is slowly added to a mixture of 50 ml. anhydrous tetrahydrofuran and 15 g. LiAlH4 while stirring over a period of 1.5 hours. After the addition is completed, the mixture is stirred under reflux and under a nitrogen atmosphere for twenty hours. After cooling to room temperature the excess reagent is destroyed by adding a mixture (45 ml.) of water and THF (1:2), followed by 15 ml. NaOH 15% and 45 ml. of water. The mixture is filtered and the filtrate is evaporated to dryness. The residue is dissolved in benzene and the solution is passed through a column of Al2O3 with benzene as eluant. The solution is evaporated to dryness and a semicrystalline product is obtained (mixture of crystals and an oil) which proves to be the desired product.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux and under a nitrogen atmosphere for twenty hours
  3. customis destroyed
  4. additionby adding a mixture (45 ml.) of water and THF (1:2)
  5. filtrationThe mixture is filtered
  6. customthe filtrate is evaporated to dryness
  7. dissolutionThe residue is dissolved in benzene
  8. customThe solution is evaporated to dryness
  9. customa semicrystalline product is obtained (
  10. additionmixture of crystals

Sources & evidence

ORD record
ord-1cbc699b1ca946738ecbec3c99ab48ba
Source dataset
uspto-grants-1976_06
Patent number
US03966766

Reaction notes

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