Potassium Carbonate → HCID 19878324, compound

HRID 1885911Notes

Reaction equation

HRID 1885911 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]4=3)[C:14]3[C:9]2=[CH:10][C:11]([O:25][CH3:26])=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.Cl.[CH2:28]([N:30]([CH2:34][CH3:35])[CH2:31][CH2:32]Cl)[CH3:29].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:26][O:25][C:11]1[CH:10]=[C:9]2[C:14]([C:15]3[C:20]([CH:8]2[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:29][CH2:28][N:30]([CH2:34][CH3:35])[CH2:31][CH3:32])=[CH:7][CH:6]=2)=[C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]2=[CH:17][CH:16]=3)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 19878336HCID 19878336, compound

Product 1

HCID 19878324HCID 19878324, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Seven grams of the product of Example 1 was combined with 5.7 g of diethyl-(2-chloroethyl)amine hydrochloride and 12.1 g of potassium carbonate in 75 ml of methyl ethyl ketone, and the mixture was stirred under reflux for 31/2 hours. The mixture was then poured into ice water, extracted twice with 300 ml portions of ethyl acetate, and the organic extract was washed with brine, dried, and evaporated under vacuum to a tan liquid. The impure product was purified by chromatography over a silica gel column, eluting with a gradient solvent beginning with 200 ml of toluene, then proceeding in 200 ml increments to 100% ethyl acetate, and finally eluting with 500 ml of 1:9 methanol:ethyl acetate. The product-containing fractions were evaporated under vacuum to obtain 3.85 g of the desired product, m.p. 109°-115° C.

Workup

  1. temperatureunder reflux for 31/2 hours
  2. extractionextracted twice with 300 ml portions of ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with brine
  5. customdried
  6. customevaporated under vacuum to a tan liquid
  7. customThe impure product was purified by chromatography over a silica gel column
  8. washeluting with a gradient solvent
  9. washfinally eluting with 500 ml of 1:9 methanol
  10. customThe product-containing fractions were evaporated under vacuum

Sources & evidence

ORD record
ord-2cfe450272d5435abc077a28d030addf
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

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