Hydrochloric Acid → (R)-1-(3-indolyl)-2-propylaminopentane hydrochloride

HRID 1925492Notes

Reaction equation

HRID 1925492 reaction equation
[ClH:1].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])=[CH:3]1>C(OCC)C>[ClH:1].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:13][CH2:14][CH3:15])=[CH:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67426163(R)-1-(3-indolyl)-2-propylaminopentane

Product 1

HCID 67427056(R)-1-(3-indolyl)-2-propylaminopentane hydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Saturated hydrogen chloride in diethyl ether (20 mL) was added to a solution of (R)-1-(3-indolyl)-2-propylaminopentane (7.13 g) in diethyl ether under ice-cooling and stirring and then stirred at the same temperature for 10 minutes. The precipitated crystals were collected by filtration and washed three times with diethyl ether (10 mL). The resulting powder (7.70 g) was suspended in acetone (20 mL), and the suspension was stirred and refluxed for 10 minutes. The resulting yellow suspension was filtered, and the crystals were washed with acetone (5 mL three times) to give (R)-1-(3-indolyl)-2-propylaminopentane hydrochloride (4.43 g, 53% yield).

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for 10 minutes
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed three times with diethyl ether (10 mL)
  5. stirringthe suspension was stirred
  6. temperaturerefluxed for 10 minutes
  7. filtrationThe resulting yellow suspension was filtered
  8. washthe crystals were washed with acetone (5 mL three times)

Sources & evidence

ORD record
ord-666dce4870324fd583d868c0bfb78ad6
Source dataset
uspto-grants-2012_05
Patent number
US08178686B2

Reaction notes

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