Ethylenediamine → HCID 13869716, compound

HRID 1770124Notes

Reaction equation

HRID 1770124 reaction equation
C(Br)(Br)Br.[CH3:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:15](OC)=O.[CH2:19]([NH2:22])[CH2:20][NH2:21].C[Al](C)C>>[NH:21]1[CH2:20][CH2:19][N:22]=[C:15]1[C:7]1[N:6]([CH3:5])[C:14]2[C:9]([CH:8]=1)=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 4

HCID 3301EthylenediamineHCID 5558BromoformHCID 258548methyl 1-methyl-1H-indole-2-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 13869716HCID 13869716, compound

Procedure

A stirred suspension of methyl 1H-indole-2-carboxylate (5.0 g), dimethyl sulphate (9 ml) and potassium carbonate (10.4 g) in dry acetone (200 ml) was heated under reflux for 24 h. After cooling to room temperature 5% ammonia solution (50 ml) was added and the mixture stirred for 2 hours. The solvent was removed in vacuo and the residue partitioned between dichloromethane and water. The organic layer was dried and the solvent evaporated to give methyl 1-methyl-1H-indole-2-carboxylate (5.4 g) as a white solid; IR (CHBr3) max 1695 cm-1. The ester was treated with ethylenediamine and trimethylaluminium as described in Example 1(a). Purification via column chromatography on silica eluting with 5% v/v methanolic ammonia in dichloromethane gave 2-(2-imidazolin-2-yl)-1-methyl-1H-indole as a white solid. The hydrochloride salt was prepared as in Example 3 and that recrystallised from ethanol/diethyl ether; mp 290°-295° C. (decomp) (Literature mp 260°-280° C. (decomp) D. J. Hlasta, D. Luttinger, M. H. Perrone, M. J. Silbernagel, S. J. Ward and D. R. Haubrich, J. Med. Chem. 1967, 30, 1555).

Workup

  1. customPurification via column chromatography on silica eluting with 5% v/v methanolic ammonia in dichloromethane

Sources & evidence

ORD record
ord-cab9ce29f29844aa8f575bed9bdb2d39
Source dataset
uspto-grants-1995_01
Patent number
US05385919

Reaction notes

Loading…