Ethylenediamine → HCID 11218424, compound

HRID 1770126Notes

Reaction equation

C(N1C2C(=CC=CC=2)C=C1C(OC)=O)CC.Cl.[NH:18]1[CH2:22][CH2:21][N:20]=[C:19]1[C:23]1[N:24]([CH2:32][CH2:33][CH3:34])[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.C[Al](C)C.C(N)CN>>[NH:20]1[CH2:21][CH2:22][N:18]=[C:19]1[C:23]1[N:24]([CH2:32][CH2:33][CH3:34])[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

Reactant 4

HCID 3301Ethylenediamine

HCID 10680285HCID 10680285, compound

HCID 16682925Trimethylaluminum

HCID 20095499HCID 20095499, compound

Product 1

HCID 11218424HCID 11218424, compound

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.

Sources & evidence

ORD record: ord-efbd35f35a204d738ecb4da5916b06d5
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05385919

Reaction notes

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