Acetic Acid → HCID 178418358, compound

HRID 1023

Reaction equation

HRID 1023 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OCC)(OCC)OCC.[CH2:24]([C:26]1[C:31]([Br:32])=[C:30]([NH2:33])[CH:29]=[CH:28][N:27]=1)[CH3:25].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)([O-])O.[Na+]>C(O)C.B(F)(F)F.CCOCC>[CH2:24]([C:26]1[C:31]([Br:32])=[C:30]([NH:33][C@H:10]2[CH2:11][CH2:12][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:8][CH2:9]2)[CH:29]=[CH:28][N:27]=1)[CH3:25]

Participants

10

Reactant 7

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 31214Ethyl orthoformateHCID 786054-PhenylcyclohexanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 545737983-Bromo-2-ethylpyridin-4-amine

Product 1

HCID 178418358HCID 178418358, compound

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

3.48 g (20 mmol) of 4-phenylcyclohexanone in 3.3 ml of ethanol are treated with 3.3 ml of triethyl orthoformate and 2 drops of boron trifluoride etherate and warmed at 50° C. for 30 min. After addition of 2.01 g (10mmol) of 2-ethyl-3-bromo-4-aminopyridine the reaction mixture is heated at 135°-140° C. for 3.5-4 hours with simultaneous removal of the low-boiling components by distillation. It is then cooled, 40 ml of dichloroethane, 3.18 g (15 mmol) of sodium triacetoxyborohydride and 0.57 ml (10 mmol) of glacial acetic acid are added, and it is heated at 50°-60° C. for 3 hours; the reaction mixture is then cooled, saturated aqueous sodium hydrogen carbonate solution is added, the 1,2-dichloroethane is evaporated and the reaction product is extracted from the aqueous phase using ethyl acetate. Purification is carried out by column chromatography. Yield: 1.46 g (41%); RF =0.59 (ethyl acetate)

Workup

  1. temperatureis heated at 135°-140° C. for 3.5-4 hours with simultaneous removal of the low-boiling components by distillation
  2. temperatureIt is then cooled
  3. temperatureit is heated at 50°-60° C. for 3 hours
  4. temperaturethe reaction mixture is then cooled
  5. customthe 1,2-dichloroethane is evaporated
  6. extractionthe reaction product is extracted from the aqueous phase
  7. customPurification

Sources & evidence

ORD record
ord-5d3b4c5598fc43c8868c332153f62858
Source dataset
uspto-grants-1998_03
Patent number
US05723450

Linked notes

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