1-Hexanamine, hydrochloride

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the insoluble solid was collected and crystallised from aqueous ethanol to give 3-cyano-1-hexylguanidine (40 g.) m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the insoluble solid was collected crystallised from aqueous ethanol

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the insoluble solid was collected and crystallised from aqueous ethanol to give 3-cyano-1-hexylguanidine (40 g.) m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the insoluble solid was collected crystallised from aqueous ethanol

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the isoluble solid was collected and crystallised from aqueous ethanol, to give 3-cyano-1-hexylguanidine, m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the isoluble solid was collected crystallised from aqueous ethanol

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the isoluble solid was collected and crystallised from aqueous ethanol, to give 3-cyano-1-hexylguanidine, m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the isoluble solid was collected crystallised from aqueous ethanol

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

Procedure: 3-Benzyloxy-2-methyl-4-pyrone is prepared as described in (C) and is reacted with ethylamine, n-propylamine, isopropylamine, n-butylamine and n-hexylamine hydrochloride under similar conditions to those described in (C) for methylamine hydrochloride. The reaction mixture is worked up and the hydroxy group deprotected as described in (C) to give the following compounds: to give the following compounds

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

Procedure: 3-Benzyloxy-2-methyl-4-pyrone is prepared as described in (C) and is reacted with ethylamine, n-propylamine, isopropylamine, n-butylamine and n-hexylamine hydrochloride under similar conditions to those described in (C) for methylamine hydrochloride. The reaction mixture is worked up and the hydroxy group deprotected as described in (C) to give the following compounds: to give the following compounds

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 50 ml of methanol were added 2.47 g of the thus obtained 1-(1-chloro-5-isoquinolinesulfonyl)-3-piperidone, 1.11 g of n-hexylamine hydrochloride and 0.50 g of sodium cyanoborohydride, followed by stirring at 20° C. for 15 hours. The methanol was removed under reduced pressure, and 50 ml of chloroform was added to the resultant product. Then, the mixture was washed twice with 50 ml each of water and then washed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution, and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a residue. The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: chloroform) to obtain 2.54 g of 1-(1-chloro-5-isoquinolinesulfonyl)-3-hexylaminopiperidine [Compound (98)]. Compound (98) was analyzed to give the following data. The methanol was removed under reduced pressure, and 50 ml of chloroform was added to the resultant product Then, the mixture was washed twice with 50 ml each of water washed once with 50 ml of a 50% aqueous sodium hydrogencarbonate solution dried with anhydrous sodium sulfate The solvent was removed under reduced pressure to obtain a residue The residue thus obtained was subjected to purification by silica gel column chromatography (Wacogel C-200, 100 g; solvent: chloroform)

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated under reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the insoluble solid was collected and crystallised from aqueous ethanol to give 3-cyano-1-hexylguanidine m.p. 103°-105°. was heated under reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the insoluble solid was collected crystallised from aqueous ethanol

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the insoluble solid was collected and crystallised from aqueous ethanol to give 3-cyano-1-hexylguanidine (40 g.) m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the insoluble solid was collected crystallised from aqueous ethanol

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

Procedure: A mixture of hexylamine hydrochloride (63.5 g.), sodium dicyanamide (44.5 g.) and butanol (200 ml.) was heated at reflux for 18 hours and then cooled. The mixture was filtered and the filtrate was evaporated to dryness. The residue was stirred with water and the isoluble solid was collected and crystallised from aqueous ethanol, to give 3-cyano-1-hexylguanidine, m.p. 103°-105°. was heated at reflux for 18 hours cooled The mixture was filtered the filtrate was evaporated to dryness the isoluble solid was collected crystallised from aqueous ethanol

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

Procedure: 3-Benzyloxy-2-methyl-4-pyrone is prepared as described in (C) and is reacted with ethylamine, n-propylamine, isopropylamine, n-butylamine and n-hexylamine hydrochloride under similar conditions to those described in (C) for methylamine hydrochloride. The reaction mixture is worked up and the hydroxy group deprotected as described in (C) to give the following compounds: to give the following compounds