Sodium Hydroxide → HCID 22675474, compound

HRID 355812Notes

Reaction equation

HRID 355812 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][N:17]([C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26]CC)=[O:25])=[CH:22][CH:21]=1)[CH2:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][N:17]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:29][CH:30]=1)[CH2:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22675472HCID 22675472, compound

Product 1

HCID 22675474HCID 22675474, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[N-(2-(2-benzyloxyphenyl)ethyl)-N-ethylamino]benzoate was dissolved in a solution of methanol (20 ml) and tetrahydrofuran (20 ml). To this solution was added aqueous 2N sodium hydroxide (10.5 ml) and the mixture heated at reflux for 24 hours; cooled and the volume reduced by evaporation to half the original volume. Water (20 ml) was added and the mixture acidified with acetic acid. The resulting solid was filtered and dried under vacuum at 60° C. to give the title product (950mg) m.p. 175° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 hours
  3. temperaturecooled
  4. customthe volume reduced by evaporation to half the original volume
  5. additionWater (20 ml) was added
  6. filtrationThe resulting solid was filtered
  7. customdried under vacuum at 60° C.

Sources & evidence

ORD record
ord-25ade0fd21f245bba60493515ebf8d11
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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