Hydrochloric Acid → N-[2-(3,4-Dihydroxyphenyl)ethyl]cyclohexanecarboxamide

HRID 267870Notes

Reaction equation

HRID 267870 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[O:9]C.B(I)(I)I.C(=O)(O)[O-].[Na+].Cl>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:15])[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 83546Borane, triiodo-HCID 516892Sodium BicarbonateHCID 703889HCID 703889, compound

Product 1

HCID 4051742N-[2-(3,4-Dihydroxyphenyl)ethyl]cyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2.0 g. of the product of Step A carboxylate in 15 ml. of methylene chloride and cool the solution to about -78°C. Add 2.5 g. of boron triiodide and allow the reaction mixture to warm up to about 0°C with vigorous stirring. Stir the reaction mixture at about 0°C overnight, then add about 10 ml. saturated sodium bicarbonate solution. Acidify the mixture with 2N hydrochloric acid and extract with ethyl acetate. Decolorize the extract with aqueous sodium thiosulfate, then wash the extract successively with 2N hydrochloric acid solution, saturated sodium bicarbonate solution, and water. Dry the extract over anhydrous sodium sulfate and evaporate to a residue. Crystallize the residue from a toluene-ethanol mixture to obtain the title product 124°C - 126°C.

Workup

  1. dissolutionDissolve 2.0 g
  2. additionAdd 2.5 g
  3. additionadd about 10 ml
  4. extractionextract with ethyl acetate
  5. extractionextract with aqueous sodium thiosulfate
  6. washwash the
  7. extractionextract successively with 2N hydrochloric acid solution, saturated sodium bicarbonate solution, and water
  8. customDry the
  9. extractionextract over anhydrous sodium sulfate
  10. customevaporate to a residue
  11. customCrystallize the residue from a toluene-ethanol mixture

Sources & evidence

ORD record
ord-30156971e95a43709326112c47dabc83
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

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