HCID 19375088, compound → HCID 19375030, compound

HRID 128793Notes

Reaction equation

HRID 128793 reaction equation
[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][CH:3]([O:21][CH3:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 19375088HCID 19375088, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19375030HCID 19375030, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-(2,2-dimethoxyethyl)phenyl)octanamide (1.11 g, prepared as in example 21) is reduced with lithium aluminum hydride (1.4 equivalents) in refluxing THF (15 ml) to provide 1-(2,2-dimethoxyethyl)-4-(octylamino)benzene as a pale yellow oil after the usual work-up. This material (0.96 g) is dissolved in dichloromethane (10 ml) and treated with acetic anhydride (0.32 ml), triethylamine (0.5 ml) and DMAP (50 mg). The mixture is stirred at room temperature for 4 hr, then washed in turn with 10% aqueous citric acid and saturated sodium bicarbonate. The organic solution is dried, filtered, and concentrated to provide N-(4-(2,2-dimethoxyethyl)phenyl)-N-octylacetamide as a colorless oil (1.05 g). This is condensed with glyoxylic acid by the method of example 2 above, to provide the title compound, mp 103°-105° after recrystallization from dichloromethane-hexane.

Sources & evidence

ORD record
ord-1065115735fa4feaa00711a21d8557db
Source dataset
uspto-grants-1995_11
Patent number
US05464865

Reaction notes

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