2-amino-1-(furan-2-yl)ethanone;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.0 g of (2-furylcarbonyl)methylamine hydrochloride, 7.6 g of sodium bicarbonate and 4.8 g of cyclohexylcarbonyl chloride are treated in the same manner as described in Preparation 1-(1). 6.5 g of N-cyclohexylcarbonyl-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 91.5% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.0 g of (2-furylcarbonyl)methylamine hydrochloride, 20.5 g of sodium bicarbonate and 11.4 g of isobutyryl chloride are treated in the same manner as described in Preparation 1-(1). 13.0 g of N-isobutyryl-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 67.0% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.0 g of (2-furylcarbonyl)methylamine hydrochloride, 10.5 g of sodium bicarbonate and 10.1 g of 4-methoxybenzoyl chloride are treated in the same manner as described in Preparation 1-(1). 11.0 g of N-(4-methoxybenzoyl)-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 85.3% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.0 g of (2-furylcarbonyl)methylamine hydrochloride, 10.5 g of sodium bicarbonate and 9.2 g of 4-methylbenzoyl chloride are treated in the same manner as described in Preparation 1-(1). 10.0 g of N-(4-methylbenzoyl)-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 83.3% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 23.4 g of (2-furylcarbonyl)methylamine hydrochloride, 29.3 g of sodium bicarbonate and 23.0 g of 4-fluorobenzoyl chloride are treated in the same manner as described in Preparation 1-(1). 24.0 g of N-(4-fluorobenzoyl)-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 66.8% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.4 g of (2-furylcarbonyl)methylamine hydrochloride, 4.4 g of sodium bicarbonate and 3.3 g of benzoyl chloride are treated in the same manner as described in Preparation 1-(1). 4.0 g of N-benzoyl-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 83.3% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 10 g of (2-furylcarbonyl)methylamine hydrochloride, 12.5 g of sodium bicarbonate, 200 ml of ethyl acetate and 100 ml of water are dropwise added 12.0 g of 4-chlorobenzoyl chloride at a temperature below 10° C. under stirring. The mixture is stirred at room temperature for 3 hours. Then, the ethyl acetate layer is collected, washed with water and dried. Said ethyl acetate layer is evaporated under reduced pressure to remove solvent. 16.0 g of N-(4-chlorobenzoyl)-(2-furylcabonyl)methylamine are thereby obtained. Yield: 98.2% at a temperature below 10° C. The mixture is stirred at room temperature for 3 hours Then, the ethyl acetate layer is collected washed with water dried is evaporated under reduced pressure to remove solvent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: U.S. Patent 2,547,712 describes a process for producing certain 1-[2-furyl]-2-aminopropane diols. In a more relevant disclosure, in Example 2 of the '712 patent, the compound 2-furyl aminomethyl ketone hydrochloride is produced by reacting a 2-furyl bromomethyl ketone hexamethylene tetraamine complex with HCl. In the next step the 2-furyl aminomethyl ketone is added to a mixture of glacial acetic acid and acetic anhydride to which is then added sodium acetate. The product of that reaction is 2-furyl acetamidomethyl ketone, which is reacted with formalin, sodium bicarbonate and methanol to form 2-furyl-α-acetamido-β-hydroxyethyl ketone. This product was then reduced to the corresponding diol with aluminum isopropoxide (the catalyst of the '913 patent) in isopropanol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: U.S. Patent 2,547,712 describes a process for producing certain 1-[2-furyl]-2-aminopropane diols. In a more relevant disclosure, in Example 2 of the '712 patent, the compound 2-furyl aminomethyl ketone hydrochloride is produced by reacting a 2-furyl bromomethyl ketone hexamethylene tetraamine complex with HCl. In the next step the 2-furyl aminomethyl ketone is added to a mixture of glacial acetic acid and acetic anhydride to which is then added sodium acetate. The product of that reaction is 2-furyl acetamidomethyl ketone, which is reacted with formalin, sodium bicarbonate and methanol to form 2-furyl-α-acetamido-β-hydroxyethyl ketone. This product was then reduced to the corresponding diol with aluminum isopropoxide (the catalyst of the '913 patent) in isopropanol.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5.0 g of (2-furylcarbonyl)methylamine hydrochloride, 7.6 g of sodium bicarbonate and 4.8 g of cyclohexylcarbonyl chloride are treated in the same manner as described in Preparation 1-(1). 6.5 g of N-cyclohexylcarbonyl-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 91.5% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 16.0 g of (2-furylcarbonyl)methylamine hydrochloride, 20.5 g of sodium bicarbonate and 11.4 g of isobutyryl chloride are treated in the same manner as described in Preparation 1-(1). 13.0 g of N-isobutyryl-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 67.0% as described in Preparation 1-(1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.0 g of (2-furylcarbonyl)methylamine hydrochloride, 10.5 g of sodium bicarbonate and 10.1 g of 4-methoxybenzoyl chloride are treated in the same manner as described in Preparation 1-(1). 11.0 g of N-(4-methoxybenzoyl)-(2-furylcarbonyl)methylamine are thereby obtained. Yield: 85.3% as described in Preparation 1-(1)