1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)-4H-3,1-benzoxazin-4-one

HRID 1373711Notes

Reaction equation

HRID 1373711 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]([NH:13][C:14]3[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=3[C:16]([OH:18])=[O:17])=O)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[O:4]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[O:17][C:16](=[O:18])[C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[N:13]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219062722-(1,4-Dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzoic Acid

Product 1

HCID 219066372-(1,4-Dioxa-8-azaspiro[4.5]decan-8-yl)-4H-3,1-benzoxazin-4-oneYield 75.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 2-(1,4-dioxa-8-azaspiro[4.5]decan-8-ylcarbonyl)aminobenzoic acid (1.91 g, 6.25 mmol) in DMF (12 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g, 6.25 mmol). After 30 min, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed consecutively with 1 M citric acid, brine, satd aq sodium bicarbonate, and brine, then dried with MgSO4, filtered and concentrated in vacuo. The residue was then suspended in diethyl ether, sonicated, filtered and dried in vacuo to give 1.36 g of the title compound; which was used without further purification.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic phase was washed consecutively with 1 M citric acid, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customsonicated
  9. filtrationfiltered
  10. customdried in vacuo

Sources & evidence

ORD record
ord-c798218724a3431a92b7b25968d44a60
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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