Sodium Chloride → HCID 20570833, compound

HRID 1577518Notes

Reaction equation

HRID 1577518 reaction equation
[OH:1][CH:2]([CH2:19][N:20]1[CH2:25][CH2:24][CH:23]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:22][CH2:21]1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14](OCC)=[O:15])[NH:9]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Na+].[OH-:42].[Na+].[O:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>>[C:48]([OH:44])(=[O:42])[C:47]1[CH:19]=[CH:2][CH:3]=[CH:45][CH:46]=1.[OH:1][CH:2]([CH2:19][N:20]1[CH2:21][CH2:22][CH:23]([CH2:26][O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[CH2:24][CH2:25]1)[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([CH2:14][OH:15])[NH:9]2

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 20570830HCID 20570830, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20570833HCID 20570833, compound

Procedure

A solution of 4.6 g. 4-{2-hydroxy-3-[4-(2-pyridyloxymethyl)-piperidino]-propoxy}-2-ethoxycarbonylindole (preparation see Example 18f) in 125 ml. anhydrous tetrahydrofuran is added dropwise to a suspension of 1 g. lithium aluminum hydride in 125 ml. anhydrous tetrahydrofuran. The reaction mixture is then stirred for 30 minutes, decomposed, while cooling, with an aqueous solution of sodium chloride and 10 N aqueous sodium hydroxide solution, filtered, washed with tetrahydrofuran and evaporated. By adding an equivalent amount of benzoic acid, there are obtained 4.0 g. (74% of theory) 4-{2-hydroxy-3-[4-(2-pyridyloxymethyl)-piperidino]-propoxy}-2-hydroxymethylindole benzoate which is recrystallized from isopropanol; m.p. 76°-78° C.

Workup

  1. filtrationfiltered
  2. washwashed with tetrahydrofuran
  3. customevaporated
  4. additionBy adding an equivalent amount of benzoic acid, there
  5. customare obtained 4.0 g
  6. custom(74% of theory) 4-{2-hydroxy-3-[4-(2-pyridyloxymethyl)-piperidino]-propoxy}-2-hydroxymethylindole benzoate which is recrystallized from isopropanol

Sources & evidence

ORD record
ord-5dc9c81fe5254c8f9a7b5fa40fda476a
Source dataset
uspto-grants-1981_09
Patent number
US04288442

Reaction notes

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