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

HRID 1158253Notes

Reaction equation

HRID 1158253 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-069a63fbc8194e9e8470f15b6995f88b
Source dataset
uspto-grants-2010_10
Patent number
US07807840B2

Reaction notes

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