2-(3,4-dimethoxyphenyl)ethanol

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:

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: A mixture of 5.0 g (0.027 mole) of 3,4-dimethoxy phenethyl alcohol in 12 ml DMF was added dropwise to a suspension of sodium hydride (1.20 g, 60% in oil; 0.09 mole) in 40 ml DMF at 0°-5° C. The suspension was stirred for 20 min under argon after which sulfamoyl chloride (3.54 g, 0.03 mole) was added portionwise at 0°-5° C. After stirring for 20 min the resultant suspension was poured into ice and extracted twice with Et2O. The combined organic phases were washed with saturated brine, dried over potassium carbonate and concentrated in vacuo to a white solid which was recrystallized in EtOAc/hexane to give 0.95 g (13%) of the title compound as a solid, mp 106°-108° C. Both 13C and 1H NMR in CDCl3 confirmed the structure. was added portionwise at 0°-5° C was poured into ice extracted twice with Et2O The combined organic phases were washed with saturated brine dried over potassium carbonate concentrated in vacuo to a white solid which was recrystallized in EtOAc/hexane

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

Procedure: The title compound, white solid, m.p. 144° C. and MS: m/e=419.5 (M+H+) was prepared in accordance with the general method of example 1 from diphenylacetyl isocyanate and 2-(3,4-dimethoxy-phenyl)-ethanol.

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

Procedure: A mixture of 200 g of 3,4-dimethoxybenzeneethanol and 163.7 g of 1-(4-piperidinyl)ethanone in 800 ml of ethanol saturated with anhydrous hydrochloric acid was stirred for 15 h at ambient temperature. The mixture was concentrated under vacuum, and the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated. After filtration the hydrochloride was dissolved in water and sodium hydroxide until the pH was 12. The base was extracted with dichloromethane, and the organic phase was washed with water, dried and evaporated to yield 251 g (86.5%) of crude 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine. The mixture was concentrated under vacuum the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated After filtration the hydrochloride was dissolved in water The base was extracted with dichloromethane the organic phase was washed with water dried evaporated

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

Procedure: A mixture of 200 g of 3,4-dimethoxybenzeneethanol and 163.7 g of 1-(4-piperidinyl)ethanone in 800 ml of ethanol saturated with anhydrous hydrochloric acid was stirred for 15 h at ambient temperature. The mixture was concentrated under vacuum, and the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated. After filtration the hydrochloride was dissolved in water and sodium hydroxide until the pH was 12. The base was extracted with dichloromethane, and the organic phase was washed with water, dried and evaporated to yield 251 g (86.5%) of crude 4-(3,4-dihydro-6,7-dimethoxy-1-methyl-1H-2-benzopyran-1-yl)piperidine. The mixture was concentrated under vacuum the concentrate was diluted with 500 ml of ethanol after which the hydrochloride precipitated After filtration the hydrochloride was dissolved in water The base was extracted with dichloromethane the organic phase was washed with water dried evaporated

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

Procedure: A mixture of 3,4-dimethoxybenzeneethanol and 62.8 g of chloroacetaldehyde diethylacetal in 1 l of absolute ethanol saturated with anhydrous hydrochloric acid, was stirred at ambient temperature for 24 h. The solvent was evaporated and 88.4 g (88.8%) of 1-chloromethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran was obtained by distillation. The solvent was evaporated

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

Procedure: A mixture of 3,4-dimethoxybenzeneethanol and 62.8 g of chloroacetaldehyde diethylacetal in 1 l of absolute ethanol saturated with anhydrous hydrochloric acid, was stirred at ambient temperature for 24 h. The solvent was evaporated and 88.4 g (88.8%) of 1-chloromethyl-3,4-dihydro-6,7-dimethoxy-1H-2-benzopyran was obtained by distillation. The solvent was evaporated