Iodoethane → HCID 23336502, compound

HRID 903605Notes

Reaction equation

HRID 903605 reaction equation
[CH2:1]([I:3])[CH3:2].[CH3:4][O:5][C:6]([CH2:8][CH2:9][CH2:10][C:11]1[C:23]2[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH2:14][CH2:13][N:12]=1)=[O:7]>>[I-:3].[CH3:4][O:5][C:6]([CH2:8][CH2:9][CH2:10][C:11]1[C:23]2[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH2:14][CH2:13][N+:12]=1[CH2:1][CH3:2])=[O:7]

Participants

3

Reactant 2

HCID 6340IodoethaneHCID 135703142HCID 135703142, compound

Product 1

HCID 23336502HCID 23336502, compound

Procedure

15 ml of ethyl iodide were added to 1.80 g of 3,4-dihydro-1-(3-methoxycarbonylpropyl)-β-carboline [cf. Rec. Trav. Chim., Vol. 84, No. 9-10, pp 1183-1199(1965)], and the mixture was stirred at 70°-80° C. overnight. After the reaction was completed, the mixture was concentrated to dryness, whereby 3,4-dihydro-1-(3-methoxycarbonylpropyl)-2-ethyl-β-carbolinium iodide was obtained as a crude product. The crude product was dissolved in 20 ml of ethanol, and one g of sodium borohydride was added thereto. The mixture was stirred at room temperature for one hour. Then, the mixture was extracted with ethyl acetate. The extract was washed with water, dried and evaporated to remove solvent. The residue thus obtained was purified by silica gel chromatography (Solvent: 5% methanol-chloroform), whereby 0.2 g of 1,2,3,4-tetrahydro-1-(3-methoxycarbonylpropyl)-2-ethyl-β-carboline was obtained. Yield: 11%

Workup

  1. concentrationthe mixture was concentrated to dryness

Sources & evidence

ORD record
ord-827ec5cea7e147a8aef4d3540b3e86d7
Source dataset
uspto-grants-1980_10
Patent number
US04228168

Reaction notes

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