Methyl Ethyl Ketone → HCID 53785807, compound

HRID 1885910Notes

Reaction equation

HRID 1885910 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.C(C(C)=O)C.C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]Cl>C(OCC)(=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][CH2:42][CH2:41][N:40]([CH3:44])[CH3:39])=[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

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 19878336HCID 19878336, compound

Product 1

HCID 53785807HCID 53785807, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

A 3.4 g portion of the compound of Example 1 was combined with 75 ml of methyl ethyl ketone, 6.1 g of potassium carbonate, and 2.45 g of dimethyl-(2-chloroethyl)amine hydrochloride. The mixture was stirred under reflux for 24 hours. After cooling to 25° C., 50 g of ice and 100 ml of ethyl acetate were added. The organic layer was separated, washed with brine, and concentrated to provide the crude product which was then purified on a silica gel column (120 mm high and 70 mm in diameter). The elution started with 500 ml of toluene, and proceeded through 300 ml increments of toluene containing from 1 to 10% triethylamine, in 1% increments. The product-containing fractions were combined and concentrated to dryness under vacuum to obtain 3.1 g of partially purified product, which was chromatographed again on a similar column, beginning with 100 ml of toluene. The gradient solvent was then changed in 100 ml increments from toluene containing 10% of 5:3 ethyl acetate:acetonitrile, to 10% of toluene in the ethyl acetate:acetonitrile mixture. Then a second gradient solvent was used, again in 100 ml increments, starting with the 5:3 ethyl acetate:acetonitrile mixture, going to the same solvent containing 10% of triethylamine. The product-containing fractions were then evaporated under vacuum to obtain 2.9 g of purified desired product, m.p. 159°-160° C.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe organic layer was separated
  3. washwashed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a559b45e9caa4c30b4e7fbe864ea4eeb
Source dataset
uspto-grants-1992_09
Patent number
US05147880

Reaction notes

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