Morpholine → HCID 22475072, compound

HRID 2184139Notes

Reaction equation

HRID 2184139 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([OH:13])=O)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.OC1C2N=NNC=2C=CC=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.Cl.CN(C)CCCN=C=NCC>C(#N)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[C:3]([C:11]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:13])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 134541656-Chloro-1,3-benzodioxole-5-carboxylic acidHCID 178418300HCID 178418300, compound

Product 1

HCID 22475072HCID 22475072, compoundYield 80.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 6-chloro-1,3-benzodioxole-5-carboxylic acid (0.49 g, 2.44 mmol) and hydroxybenzotriazole (66 mg, 0.49 mmol) in acetonitrile (20 mL) were added morpholine (0.53 mL, 6.1 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.52 g, 2.7 mmol). The orange solution was stirred 72 h at room temperature, diluted with ethyl acetate and poured into water. The phases were separated and the aqueous phase extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel to afford the title compound as white solid (0.53 g, 80%), mp 155° C.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1a1cdcb36108439c9346029be6af8174
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

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