Water → 3-(3-hydroxypropyl)-N-(3-pyridyl)indole

HRID 485342Notes

Reaction equation

HRID 485342 reaction equation
[CH:1]([CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1)=[O:2].[H-].C([Al+]CC(C)C)C(C)C.O>C(Cl)Cl.C1(C)C=CC=CC=1>[OH:2][CH2:1][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 134903543-(2-formylethyl)-N-(3-pyridyl)indoleHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 202702043-(3-hydroxypropyl)-N-(3-pyridyl)indole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of 3-(2-formylethyl)-N-(3-pyridyl)indole in 15 ml of methylene chloride under nitrogen is cooled to -20° and 4.6 ml of 1.75M diisobutylaluminum hydride in toluene is added dropwise. The reaction is allowed to warm to room temperature for 2 hours and 20 ml of water is added with vigorous stirring. The reaction mixture is filtered through celite which is further washed with methylene chloride. The organic phase is separated, dried over potassium carbonate and evaporated to yield 3-(3-hydroxypropyl)-N-(3-pyridyl)indole as an oil; IR (CH2Cl2) 3480 cm-1.

Workup

  1. filtrationThe reaction mixture is filtered through celite which
  2. washis further washed with methylene chloride
  3. customThe organic phase is separated
  4. dry with materialdried over potassium carbonate
  5. customevaporated

Sources & evidence

ORD record
ord-b62fe4eb57014898bda6c61f3435dd6b
Source dataset
uspto-grants-1985_08
Patent number
US04536505

Reaction notes

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