Sodium Hydroxide → HCID 57285652, compound

HRID 648660Notes

Reaction equation

HRID 648660 reaction equation
[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([CH:17]([C:29]([NH2:31])=[O:30])[C:18]2[CH:28]=[CH:27][C:21]([C:22](OCC)=[O:23])=[CH:20][CH:19]=2)[CH2:14][CH2:15][CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[N:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:13]([CH:17]([C:29]([NH2:31])=[O:30])[C:18]2[CH:19]=[CH:20][C:21]([CH2:22][OH:23])=[CH:27][CH:28]=2)[CH2:14][CH2:15][CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 20145118HCID 20145118, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 57285652HCID 57285652, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.0 gm (11.83 m mol) of ethyl 4-[(1-(2-piperidino-phenyl)-1-butyl)-aminocarbonylmethyl]-benzoate in 75 ml of absolute tetrahydrofuran was added dropwise, at an internal temperature of 0° C., to a stirred suspension of 0.68 gm (17.95 m mol) of lithium aluminium hydride in 25 ml of absolute tetrahydrofuran. The mixture was stirred for 20 hours at ambient temperature and then cooled to 0° C., and 4N sodium hydroxide solution was slowly added dropwise thereto until a filterable precipitate formed. The mixture was filtered, and the precipitate was decocted several times with ether. The combined organic solutions were concentrated by evaporation in vacuo. The evaporation residue was distributed between water and ether. The ether phase was dried, filtered, and concentrated by evaporation in vacuo. The evaporation residue was purified by column chromatography on silica gel [toluene/acetone (5:1)].

Workup

  1. temperaturecooled to 0° C.
  2. customuntil a filterable precipitate formed
  3. filtrationThe mixture was filtered
  4. concentrationThe combined organic solutions were concentrated by evaporation in vacuo
  5. dry with materialThe ether phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation in vacuo
  8. customThe evaporation residue was purified by column chromatography on silica gel [toluene/acetone (5:1)]

Sources & evidence

ORD record
ord-d4e62fc588d44899a207ba65363bfa9e
Source dataset
uspto-grants-1988_04
Patent number
US04735959

Reaction notes

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