Ethanol → HCID 13747434, compound

HRID 1034020Notes

Reaction equation

HRID 1034020 reaction equation
[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]([NH:18][CH:19]([CH2:32][OH:33])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[H-].[Na+].[CH2:36](I)[CH3:37].C(O)C>O1CCCC1>[CH2:1]([O:3][C:4]1[CH:14]=[C:13]([CH2:15][C:16]([NH:18][CH:19]([CH2:32][O:33][CH2:36][CH3:37])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]2)=[O:17])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 13747418HCID 13747418, compound

Product 1

HCID 13747434HCID 13747434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-ethoxy-4-[N-(α-hydroxymethyl-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate (0.64 g, 1.4 mmol) is added with stirring at ambient temperature to sodium hydride (0.061 g, 1.4 mmol) (55% in oil) in absolute tetrahydrofuran (6.4 ml). The mixture is stirred for 1 hour, then ethyl iodide (0.113 ml, 1.4 mmol) is added and the mixture is stirred for a further 16 hours at ambient temperature. Then ethanol (2 ml) is added and the mixture is evaporated down in vacuo. The evaporation residue is partitioned between chloroform and water. The organic phase is washed twice with water, dried, filtered and concentrated by evaporation in vacuo. The evaporation residue is purified by column chromatography on silica gel (chloroform/acetone=17/3).

Workup

  1. stirringthe mixture is stirred for a further 16 hours at ambient temperature
  2. customthe mixture is evaporated down in vacuo
  3. customThe evaporation residue is partitioned between chloroform and water
  4. washThe organic phase is washed twice with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe evaporation residue is purified by column chromatography on silica gel (chloroform/acetone=17/3)

Sources & evidence

ORD record
ord-6b4fd4bfaf604c5ebfcb15729e52e987
Source dataset
uspto-grants-1994_05
Patent number
US05312924

Reaction notes

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