Potassium Carbonate → HCID 20198285, compound

HRID 652044Notes

Reaction equation

HRID 652044 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[CH3:14][Si:15]([CH3:32])([CH3:31])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[CH3:14][Si:15]([CH3:31])([CH3:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 225219p-Aminophenylacetic acid ethyl esterHCID 20198239HCID 20198239, compound

Product 1

HCID 20198285HCID 20198285, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8.2 g. of 4-aminophenylacetic acid, 150 ml. of absolute ethanol, and 3 ml. of boron trifluoride etherate is heated to reflux for 15 hours. The solution is concentrated by distillation and then evaporated to dryness in vacuo. The residue is dissolved in ethyl ether, washed with aqueous sodium bicarbonate, dried, and evaporated to yield ethyl 4-aminophenylacetate. A mixture of 5.0 g. of this amine, 9.7 g. of 14-(trimethylsilyl)tetradecyl bromide, 4.2 g. of anhydrous potassium carbonate and 40 ml. of hexamethylphosphoramide is heated at 80° C. for 7 hours. The mixture is then cooled, diluted with water, and extracted with ethyl ether. The ether extracts are washed with water, dried and evaporated. The residue is recrystallized yielding ethyl 4-[14-(trimethylsilyl)tetradecylamino]phenylacetate. A mixture of 6.0 g. of this ester, 7.0 g. of potassium hydroxide and 100 ml. of ethanol-water is heated to reflux for 4 hours. While hot, the mixture is adjusted to pH 7 with concentrated hydrochloric acid.. The mixture is diluted with water, cooled and filtered. Recrystallization of the precipitate yields the title product as a white solid.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureThe mixture is then cooled
  3. extractionextracted with ethyl ether
  4. washThe ether extracts are washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized

Sources & evidence

ORD record
ord-f7ba1f4cfa7e41baad019cedc9f7202a
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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