6-bromohexoxymethylbenzene

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: Ethyl 2-ethoxycarbonyl-8-benzyloxyoctanoate was prepared from 6-benzyloxyhexyl bromide (3.52 g, 13 mmol) and diethyl malonate (2.29 g, 14 mmol) according to the general procedure given above. Yield 60%, bp 152-158° C./0.15 torr. 1H-NMR: 1.24 (t, 6H), 1.2-1.9 (m, 10H), 3.43 (t, 2H), 4.18 (q, 4H), 4.45 (s, 2H), 7.27 (m, 5H).

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

Procedure: 6-Benzyloxyhexyl bromide was prepared from benzyl alcohol (4.75 g, 44 mmol) and 1,6-dibromohexane (9.76 g, 40 mmol) using the general procedure given above. Yield: 36%, bp 100-105° C./torr: 1H-NMR: 1.2-1.9 (m, 8H), 3.37 (t, 4H), 4.46 (s, 2H), 7.28 (m, 5H).

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

Procedure: 4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (1.00 g) as starting compound and 6-benzyloxyhexyl bromide (0.75 g) were reacted and treated in the same manner as in Example 168 to give 0.45 g of 4-amino-N-((1-(6-benzyloxyhexyl)piperidin-4-yl)methyl)-5-chloro-2-methoxybenzamide. were reacted treated in the same manner as in Example 168

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

Procedure: To a suspension of sodium hydride in 1,4-dioxane was added benzyl alcohol in 1,4-dioxane over a period of 30 minutes at 80° C., and the mixture was stirred for 1 hour. The obtained alkoxide solution was added to a solution of 1,6-dibromohexane in 1,4-dioxane at room temperature. The mixture was stirred at 80° C. for 14 hours and insoluble materials were filtered off. The filtrate was concentrated and the residue was distilled under reduced pressure to give the object compound. The mixture was stirred at 80° C. for 14 hours insoluble materials were filtered off The filtrate was concentrated the residue was distilled under reduced pressure to give the object compound

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

Procedure: To a suspension of sodium hydride in 1,4-dioxane was added benzyl alcohol in 1,4-dioxane over a period of 30 minutes at 80° C., and the mixture was stirred for 1 hour. The obtained alkoxide solution was added to a solution of 1,6-dibromohexane in 1,4-dioxane at room temperature. The mixture was stirred at 80° C. for 14 hours and insoluble materials were filtered off. The filtrate was concentrated and the residue was distilled under reduced pressure to give the object compound. The mixture was stirred at 80° C. for 14 hours insoluble materials were filtered off The filtrate was concentrated the residue was distilled under reduced pressure to give the object compound

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

Procedure: Ethyl 2-ethoxycarbonyl-8-benzyloxyoctanoate was prepared from 6-benzyloxyhexyl bromide (3.52 g, 13 mmol) and diethyl malonate (2.29 g, 14 mmol) according to the general procedure given above. Yield 60%, bp 152-158° C./0.15 torr. 1H-NMR: 1.24 (t, 6H), 1.2-1.9 (m, 10H), 3.43 (t, 2H), 4.18 (q, 4H), 4.45 (s, 2H), 7.27 (m, 5H).

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

Procedure: 6-Benzyloxyhexyl bromide was prepared from benzyl alcohol (4.75 g, 44 mmol) and 1,6-dibromohexane (9.76 g, 40 mmol) using the general procedure given above. Yield: 36%, bp 100-105° C./torr: 1H-NMR: 1.2-1.9 (m, BH), 3.37 (t, 4H), 4.46 (s, 2H), 7.28 (m, 5H).

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

Procedure: 6-Benzyloxyhexyl bromide was prepared from benzyl alcohol (4.75 g, 44 mmol) and 1,6-dibromohexane (9.76 g, 40 mmol) using the general procedure given above. Yield: 36%, bp 100-105° C./torr: 1H-NMR: 1.2-1.9 (m, BH), 3.37 (t, 4H), 4.46 (s, 2H), 7.28 (m, 5H).

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

Procedure: Ethyl 2-ethoxycarbonyl-8-benzyloxyoctanoate was prepared from 6-benzyloxyhexyl bromide (3.52 g, 13 mmol) and diethyl malonate (2.29 g, 14 mmol) according to the general procedure given above. Yield 60%, bp 152°-158° C./0.15 torr. 1H-NMR: 1.24 (t, 6H), 1.2-1.9 (m, 10H), 3.43 (t, 2H), 4.18 (q, 4H), 4.45 (s, 2H), 7.27 (m, 5H).

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

Procedure: 6-Benzyloxyhexyl bromide was prepared from benzyl alcohol (4.75 g, 44 mmol) and 1,6-dibromohexane (9.76 g, 40 mmol) using the general procedure given above. Yield: 36%, bp 100°-105° C./torr: 1H-NMR: 1.2-1.9 (m, 8H), 3.37 (t, 4H), 4.46 (s, 2H), 7.28 (m, 5H).