Ethanol → HCID 13747434, compound

HRID 567609Notes

Reaction equation

HRID 567609 reaction equation
C([C:3]1[CH:13]=[C:12]([CH2:14][C:15]([NH:17][CH:18]([CH2:31][OH:32])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:16])[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])C.[H-].[Na+].[CH2:35](I)[CH3:36].[CH2:38]([OH:40])[CH3:39]>O1CCCC1>[CH2:38]([O:40][C:3]1[CH:13]=[C:12]([CH2:14][C:15]([NH:17][CH:18]([CH2:31][O:32][CH2:35][CH3:36])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:16])[CH:11]=[CH:10][C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:39]

Participants

6

Reactant 4

HCID 702EthanolHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 21261783HCID 21261783, compound

Product 1

HCID 13747434HCID 13747434, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-ethyl-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-9355f913e0354551b525d87577bd0134
Source dataset
uspto-grants-2001_01
Patent number
USRE037035E1

Reaction notes

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