2,2,6-Trimethyl-4H-1,3-dioxin-4-one → HCID 14801608, compound

HRID 2107874Notes

Reaction equation

HRID 2107874 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[CH:8][C:9]([O:11][CH3:12])=[O:10].CC1(C)[O:19][C:18](=O)[CH:17]=[C:16]([CH3:21])O1>C1(C)C(C)=CC=CC=1>[CH3:21][C:16]1[N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]2=[C:8]([C:9]([O:11][CH3:12])=[O:10])[C:18](=[O:19])[CH:17]=1

Participants

4

Reactant 2

HCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-oneHCID 67871225Methyl (azepan-2-ylidene)acetate

Product 1

HCID 14801608HCID 14801608, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture of 20.0 g of methyl α-(hexahydro-2-azepinylidene)acetate and 77 ml of xylene was gently refluxed, to which a mixture of 41.9 g of 2,2,6-trimethyl-4H-1,3-dioxin-4-one and 41 ml of xylene was dropwise added taking 45 minutes and refluxed for 2 hours, removing the by-product acetone through a Dean-Stark apparatus. The reaction mixture was cooled to room temperature. The resulting crystals were filtered, washed and dried to afford 21.4 g (Yield 77%) of methyl 2,6,7,8,9,10-hexahydro-4-methyl-2-oxo-pyrido[1,2-a]azepine-1-carboxylate.

Workup

  1. temperaturewas gently refluxed, to which
  2. additionwas dropwise added
  3. temperaturerefluxed for 2 hours
  4. customremoving the by-product acetone through a Dean-Stark apparatus
  5. filtrationThe resulting crystals were filtered
  6. washwashed
  7. customdried

Sources & evidence

ORD record
ord-8fef781350ce4a4b87c98ca361f94ac4
Source dataset
uspto-grants-1990_06
Patent number
US04936121

Reaction notes

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