Process for the production of substituted 2-[2-(phenyl) ethylamino]alkaneamide derivatives
An alkyl and group technology, applied in the field of 2-[2-ethylamino]alkanoic amide derivatives, can solve the problems of industrial level amplification, low total yield, danger and the like
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Examples
Embodiment 1
[0080] Synthesis of 3-butoxybenzaldehyde
[0081]
[0082] A mixture containing 3.95kg (32.34mol) of 3-hydroxybenzaldehyde, 4.49kg (48.52mol) of 1-chlorobutane and 6.26kg (45.28mol) of potassium carbonate in 19.75L of N,N-dimethylformamide Heat to 115-118° C. and maintain at this temperature until the reaction is complete (3-hydroxybenzaldehyde about 0.1% area %). The reaction mixture was cooled to about 20°C. A mixture of 32.4 L of tert-butyl methyl ether and 52.9 L of water was added to the slurry, followed by stirring for 15 minutes. The biphasic mixture was allowed to separate. The organic solution was washed with aqueous sodium chloride. The batch was concentrated under reduced pressure at <50 °C to obtain 5.57 kg of the oily product 3-butoxybenzaldehyde in 96.6% molar yield.
Embodiment 2
[0084] Synthesis of 3-butoxybenzaldehyde
[0085]
[0086] The solution containing 3-hydroxybenzaldehyde 25kg (204.7mol), potassium carbonate 39.5kg (285.8mol) and 1-chlorobutane 28.5kg (307.8mol) in N,N-dimethylformamide 120kg is heated to 115°C and maintained at this temperature until the reaction is complete (3-hydroxybenzaldehyde less than 1%). The mixture was allowed to cool, diluted with 325 kg of water and concentrated in vacuo to about 325 L. The batch was diluted with 126 kg of water and 150 kg of methyl tert-butyl ether was added at about 20°C. The aqueous layer was discarded and the batch was washed with dilute sodium chloride solution followed by water. The batch was concentrated in vacuo and residual methyl tert-butyl ether was replaced with tetrahydrofuran through a series of dilutions and vacuum concentration. 33.5 kg (188.0 mol) of 3-butoxybenzaldehyde were obtained (91% molar yield, purity 99.7%).
[0087] MS (M+1:179.1); 1 H NMR is consistent with the...
Embodiment 3
[0089] Synthesis of α-Hydroxy-3-butoxyphenylacetonitrile
[0090]
[0091] 32% HCl 4.34 kg (38.11 mol) was added to a solution of sodium cyanide 1.79 kg (36.53 mol) in water 4.18 L and 3-butoxybenzene at 0-5° C. with stirring within 6 hours In a two-phase mixture composed of a solution of 5.43kg (36.59mol) of formaldehyde in 7.94L of tert-butyl methyl ether (TBME). The mixture was maintained at 0-5 °C until the reaction was complete ( 1 H-NMR showed residual 3-butoxybenzaldehyde 2-3% by weight). The mixture was warmed to 18-25°C, then diluted with 11.5 L of tert-butyl methyl ether. The two phases are separated.
[0092] The organic solution was washed with water followed by saturated aqueous sodium chloride. The organic solution was added to a solution of 0.027 kg of oxalic acid in 11.7 L of methanol. Displacing the solvent with methanol by cycles of several dilutions (with methanol) and concentrating the mixture under reduced pressure at <50°C afforded 6.16 kg (24.31 ...
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