Ethanolamine → HCID 18914376, compound

HRID 1292093Notes

Reaction equation

HRID 1292093 reaction equation
Cl.OCCN[C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH3:16])[CH:7]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([CH3:28])[CH:19]=1.[CH2:29]([CH2:31][NH2:32])[OH:30]>CN(C=O)C>[CH3:28][C:20]1([NH:32][CH2:31][CH2:29][O:30][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]([CH3:16])[CH:7]=2)[CH:19]=[CH:18][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 779734-Chloro-2-methylquinolineHCID 9549459HCID 9549459, compound

Product 1

HCID 18914376HCID 18914376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Methyl-quinolin-2-yl)-[2-(2-methyl-quinolin-4-yloxy)-ethyl]amine ##STR56## 0.72 g (2.9 mmol) of 4-(2-hydroxyethyl)amino-2-methylquinoline hydrochloride, obtained from 4-chloroquinaldine and ethanolamine, in 20 ml of absolute DMF are treated with 100 mg (3.2 mmol) of 80% pure sodium hydride in paraffin under argon. After the mixture has been stirred for 1 hour at 50° , a further 0.3 g of 4-chloroquinaldine is added. After the mixture has been stirred for 20 hours at 50°, a further 100 mg of sodium hydride, as above, are added, and the mixture is stirred for a further 18 hours. The reaction batch is concentrated. Flash chromatography (silica gel K60; methylene chloride, then methylene chloride/ethanol/ammonia 100:10:1) gives a crude product which is purified by recrystallization from isopropanol. This gives 122 mg (22%) of colorless crystals, m.p. 247°-248° C.

Sources & evidence

ORD record
ord-427226954ed142ebaea6a4af2f338bea
Source dataset
uspto-grants-1998_05
Patent number
US05756517

Reaction notes

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