1-N,2-N,2-N-trimethylcyclohexane-1,2-diamine

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)-cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)-cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C--N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C--N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)-cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C--N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C--N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 804, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g

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

Procedure: A solution of the N-formyl-N-[2-(dimethylamino)cyclohexanediamine (4 g.; 0.0235 mole) in 50 ml. of ether was added during 5 minutes to a solution of LAH (4 g.) in 250 ml. of ether and refluxed 17 hours. It was cooled in ice, and decomposed in succession with 4 ml. of H2O, 4 ml. of 15% NaOH, 12 ml. of H2O, stirred 1 hour at room temperature and filtered. The cake was washed with ether, and the ether was distilled. The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g. (82% yield). ir NH 3680 v.w., 3320; CH 2940, 2820; N-alkyl 2780; CH 1475, 1450; C-N/other 1270, 1155, 1145, 1125, 1060, 1045, 1005, 870, 805, 775. nmr in CDCl3 (60 MHz) was in accord. Mass spectrum M+ 156. It was cooled in ice filtered The cake was washed with ether the ether was distilled The titled amine (B) residue was distilled at 14 mm, b.p. 86°-87°, 3 g