[4-(2-chloro-2-oxoethyl)phenyl] acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To an ice-cold solution of 1-propylamine (9 g) in water (50 ml) was added solution of 4-acetoxyphenylacetyl chloride (10.6 g) in diethyl ether (100 ml), keeping the temperature of the mixture between 15° and 250° C. with external cooling. The ether layer was separated, washed with brine and evaporated to give N-(1-propyl)-4-acetoxyphenylacetamide as a pale yellow oil, essentially pure by TLC, which was used without further purification or characterisation. the temperature of the mixture between 15° and 250° C. The ether layer was separated washed with brine evaporated

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To an ice-cold solution of 1-propylamine (9 g) in water (50 ml) was added solution of 4-acetoxyphenylacetyl chloride (10.6 g) in diethyl ether (100 ml), keeping the temperature of the mixture between 15° and 250° C. with external cooling. The ether layer was separated, washed with brine and evaporated to give N-(1-propyl)-4-acetoxyphenylacetamide as a pale yellow oil, essentially pure by TLC, which was used without further purification or characterisation. the temperature of the mixture between 15° and 250° C. The ether layer was separated washed with brine evaporated

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

Procedure: To an ice-cold solution of 1-propylamine (9 g) in water (50 ml) was added solution of 4-acetoxyphenylacetyl chloride (10.6 g) in diethyl ether (100 ml), keeping the temperature of the mixture between 15° and 250° C. with external cooling. The ether layer was separated, washed with brine and evaporated to give N-(1-propyl)-4-acetoxyphenylacetamide as a pale yellow oil, essentially pure by TLC, which was used without further purification or characterisation. the temperature of the mixture between 15° and 250° C. The ether layer was separated washed with brine evaporated

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

Procedure: To a solution of phosgene in toluene (20% w/w, 2.2 mL, 4.2 mmol), cooled in an ice bath, was added dropwise a solution of 60 (321 mg, 1.9 mmol) in 2 mL of toluene. The mixture was stirred in the same bath, which was left to come to room temperature on its own. After 18 h, the mixture was concentrated in vacuo to give 61, which was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 2.30 (s, 3H), 5.28 (s, 2H), 7.13 (d, J=8.6 Hz, 2H), 7.42 (d, J=8.7 Hz, 2H). was left to come to room temperature on its the mixture was concentrated in vacuo

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

Procedure: Using the procedure described in Example 12, 15.0 g of 1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline was reacted with 4-acetoxyphenylacetyl chloride to give 13.0 g of N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline.

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

Procedure: To a stirred solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (20.0 g, 0.097 m) and triethylamine (9.8 ml, 0.097 m) in chloroform (200 ml) under nitrogen was added dropwise a solution of 4-acetoxyphenylacetyl chloride (20.3 g, 0.097 m) in 50 ml chloroform and the mixture stirred at ambient temperature for 16 hours. The mixture was washed with 10% HCl (3×200 ml), water (200 ml), saturated sodium carbonate (3×150 ml) and water (200 ml) and the chloroform layer dried over MgSO4. Evaporation of the solvent afforded 33.0 g of N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as a pale yellow oil (89% yield). The mixture was washed with 10% HCl (3×200 ml), water (200 ml), saturated sodium carbonate (3×150 ml) and water (200 ml) the chloroform layer dried over MgSO4 Evaporation of the solvent