Hydrochloric Acid → HCID 10680285, compound

HRID 1770125Notes

Reaction equation

HRID 1770125 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].Br[CH2:17][CH2:18][CH3:19].Cl>CS(C)=O>[CH2:17]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11])[CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 70992Methyl 1H-indole-2-carboxylate

Product 1

HCID 10680285HCID 10680285, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of methyl 1H-indole-2-carboxylate (5.0 g) and sodium hydride (60% dispersion in oil, 1.3 g) in dry dimethylsulphoxide was stirred at 60° C. for 30 minutes. The reaction mixture was cooled to room temperature before adding 1-bromopropane (2.85 ml) and then heated at 60°-80° C. for 3 hours. The cooled reaction mixture was poured into dilute hydrochloric acid and extracted with diethyl ether. The combined organic extracts were washed with water, dried (MgSO4) and the solvent removed in vacuo. The crude product was purified by chromatography on silica, and elution with 10% v/v diethyl ether in petroleum ether (bp 40°-60° C.) gave methyl 1-propyl-1H-indole-2-carboxylate (5.23 g) as a clear oil; NMR (CDCl3) δ0.93 (3H,t,J=7 Hz, C--CH3), 1.82 (2H, sext,J=7 Hz,C--CH2 --C), 3.89 (3H,s,OCH3), 4.52 (2H,t,J=7 Hz, N--CH2), 7.15 (4H,m,Ar--H), 7.67 (1H,m,Ar--H). The ester was converted to 2-(2-imidazolin-2-yl)-1-propyl-1H-indole hydrochloride using trimethylaluminium and ethylenediamine as described in Example 1(a); mp 186.5°-187° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureheated at 60°-80° C. for 3 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with diethyl ether
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by chromatography on silica, and elution with 10% v/v diethyl ether in petroleum ether (bp 40°-60° C.)

Sources & evidence

ORD record
ord-c73ef21a71c3484ea93871aba8509fa6
Source dataset
uspto-grants-1995_01
Patent number
US05385919

Reaction notes

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