Water → HCID 20088003, compound

HRID 275361Notes

Reaction equation

HRID 275361 reaction equation
CO[C:3]([NH:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[C:16]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[CH:15]2)[CH2:10][CH2:9]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH3:3][NH:5][CH2:6][CH2:7][N:8]1[CH2:9][CH2:10][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=3)[C:16]([C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[CH:15]2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 20087994HCID 20087994, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20088003HCID 20088003, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the crude 1-(1-(N-methoxycarbonyl-2-aminoethyl)-4-piperidyl)-3-(4-fluorophenyl)-5-methyl-1H-indole (8.8 g) in dry tetrahydrofuran (75 ml) was added to a suspension of lithium aluminum hydride (2 g) in dry tetrahydrofuran (75 ml) during 15 min and the reaction mixture was refluxed for 1.5 h. After cooling on an ice bath water (4 ml), 4N aqueous NaOH (2.5 ml) and water (10 ml) were added, succesively. The precipitate was filtered off, the solution was dried (Na2SO4) and the solvents were evaporated. This afforded the title compound, as an oil Yield: 6.9 g.

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 h
  2. additionwere added
  3. filtrationThe precipitate was filtered off
  4. dry with materialthe solution was dried (Na2SO4)
  5. customthe solvents were evaporated

Sources & evidence

ORD record
ord-581ac795692a40c58a0527e9f021a5a6
Source dataset
uspto-grants-1995_02
Patent number
US05393761

Reaction notes

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