Hydrochloric Acid → HCID 20145311, compound

HRID 648665Notes

Reaction equation

HRID 648665 reaction equation
[C:1]([CH:3]([CH:16]([C:28]([NH2:30])=[O:29])[C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)#[N:2].[OH-].[Na+].Cl>O1CCOCC1>[C:1]([CH:3]([CH:16]([C:28]([NH2:30])=[O:29])[C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20145272HCID 20145272, compound

Product 1

HCID 20145311HCID 20145311, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

One and one-half grams (3.7 m mol) of ethyl 4-[(α-cyano-2-piperidino-benzyl)-aminocarbonylmethyl]-benzoate in 15 ml of dioxane were stirred together with 3.7 ml of 1N sodium hydroxide solution for 45 minutes in a bath at 60° C. and for a further 45 minutes in a bath at 80° C. After cooling with ice, the mixture was combined with 3.7 ml of 1N hydrochloric acid, the dioxane was evaporated off in vacuo, and the residue was distributed between water and chloroform. The organic solution was extracted with a small amount of water, dried, filtered, and concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel [chloroform/ethanol (5:1)].

Workup

  1. temperatureAfter cooling with ice
  2. customthe dioxane was evaporated off in vacuo
  3. extractionThe organic solution was extracted with a small amount of water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation in vacuo
  7. customThe evaporation residue was purified by column chromatography on silica gel [chloroform/ethanol (5:1)]

Sources & evidence

ORD record
ord-21a369d2c5a24e48bc91f8c609395a3b
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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