Hydrochloric Acid → HCID 22675472, compound

HRID 355813Notes

Reaction equation

HRID 355813 reaction equation
[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=1[CH2:11][C:12]([N:14]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1)[CH2:15][CH3:16])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:31]=[CH:30][CH:29]=[CH:28][C:10]=1[CH2:11][CH2:12][N:14]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=1)[CH2:15][CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22675470HCID 22675470, compound

Product 1

HCID 22675472HCID 22675472, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[N-(2-benzyloxybenzylcarbonyl)-N-ethylamino]benzoate (8.1 g) was dissolved in THF (20 ml) and 1M borane tetrahydrofuran complex added. The reaction mixture was heated at reflux for 1 hour and cooled. 2N Hydrochloric acid (20 ml) was added. The volume of the reaction mixture was reduced to half the original by evaporation. Water (100 ml) was added and made basic (pH 8) by the addition of solid potassium carbonate and the mixture extracted with diethyl ether (3×30 ml). The combined extracts were dried over MgSO4 and evaporated. The residue was purified by MPLC, eluting with 1:1 dichloromethane/hexane, to give ethyl 4-[N-(2-(2-benzyloxyphenyl)ethyl)-N-ethylamino]benzoate (1.8 g) m.p. 76° C.

Workup

  1. addition1M borane tetrahydrofuran complex added
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for 1 hour
  4. temperaturecooled
  5. customoriginal by evaporation
  6. additionWater (100 ml) was added
  7. additionby the addition of solid potassium carbonate
  8. extractionthe mixture extracted with diethyl ether (3×30 ml)
  9. dry with materialThe combined extracts were dried over MgSO4
  10. customevaporated
  11. customThe residue was purified by MPLC
  12. washeluting with 1:1 dichloromethane/hexane

Sources & evidence

ORD record
ord-462f87300dc24f1fb947492cfaa490a6
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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