Ammonium Chloride → HCID 20400811, compound

HRID 1980855Notes

Reaction equation

HRID 1980855 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([CH3:27])[C:18]=1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=O)C.[Cl-].[NH4+]>O1CCCC1>[ClH:26].[OH:9][CH2:10][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Cl:26])[CH:24]=2)[N:19]([CH3:27])[C:18]=1[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20400800HCID 20400800, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20400811HCID 20400811, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.49 g of lithium aluminum hydride in 50 ml of anhydrous tetrahydrofuran under nitrogen is added dropwise at room temperature a solution of 4.09 g of 3-(5-ethoxycarbonylpentyl)-5-chloro-1-methyl-2-(3-pyridyl)indole in 30 ml of anhydrous tetrahydrofuran. After addition is complete the suspension is stirred for 1 hour at room temperature, and 50 ml of a saturated ammonium chloride solution is added. The reaction mixture is allowed to stand at room temperature overnight and the organic layer is separated. The aqueous layer is filtered to remove salts and extracted with ethyl acetate (2×50 ml). The combined organic layers are washed with saturated brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is purified by trituration with hexane/ether and dissolved in ethanol. Ethanolic hydrochloric acid is added to acidity and the solution diluted with anhydrous ether to crystallize the product. 3-(6-Hydroxyhexyl)-5-chloro-1-methyl-2-(3-pyridyl)indole hydrochloride is obtained.

Workup

  1. additionAfter addition
  2. waitto stand at room temperature overnight
  3. customthe organic layer is separated
  4. filtrationThe aqueous layer is filtered
  5. customto remove salts
  6. extractionextracted with ethyl acetate (2×50 ml)
  7. washThe combined organic layers are washed with saturated brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe crude product is purified by trituration with hexane/ether
  11. dissolutiondissolved in ethanol
  12. additionEthanolic hydrochloric acid is added to acidity
  13. additionthe solution diluted with anhydrous ether
  14. customto crystallize the product

Sources & evidence

ORD record
ord-00585e640dbe448d804249aeadebabd2
Source dataset
uspto-grants-1985_04
Patent number
US04511573

Reaction notes

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