Hydrochloric Acid → HCID 19369856, compound

HRID 849036Notes

Reaction equation

HRID 849036 reaction equation
[OH:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([O:20][CH3:21])[C:5]2[O:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15](O)=[O:16])([CH3:10])[CH2:7][C:6]=2[C:18]=1[CH3:19].[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[OH:1][C:2]1[C:3]([O:22][CH3:23])=[C:4]([O:20][CH3:21])[C:5]2[O:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[O:16])([CH3:10])[CH2:7][C:6]=2[C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19369859HCID 19369859, compound

Product 1

HCID 19369856HCID 19369856, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution (25 ml) of 5-(2,3-dihydro-5-hydroxy-6,7-dimethoxy-2,4-dimethylbenzofuran-2-yl)valeric acid (2.0 g), morpholine (0.81 ml) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.4 g) in N,N-dimethylformamide was stirred under an atmosphere of argon at room temperature for 2 hours. The reaction mixture was made acidic by adding 1N hydrochloric acid to the mixture, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) to obtain the title compound (2.1 g, 85%) as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-525602420a534ba096c433d63733b509
Source dataset
uspto-grants-2000_01
Patent number
US06011046

Reaction notes

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