Hydrochloric Acid → HCID 22675472, compound

HRID 1006051Notes

Reaction equation

HRID 1006051 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 IM 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. additionIM 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-a950b13c68264638820772e9a1be4aa0
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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