N-[(2,3-dimethylphenyl)methyl]cyclopropanamine

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: 1B was synthesized from 2,3-dimethylbenzaldehyde (5.0 g, 37.3 mmol) using the procedure described for 1A. Yield: 6.0 g (92%) as light yellow oil. ESI-MS:m/z 176.3 (M+H)+, HPLC retention time: T=1.340 min (FAST-2). T=1.340 min (FAST-2)

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

Procedure: A mixture of 2,3-dimethylbenzaldehyde (1 eq.), cyclopropylamine (1.2 eq.) and sodium bicarbonate (1.5 eq.) were heated at reflux in MeOH (0.5 M) for 1 h. The reaction mixture was then cooled in ice and sodium borohydride (1.2 eq.) was introduced portionwise. Following the completion of addition, the reaction mixture was warmed to RT and stirred at RT for 1 h. The volatiles were then removed in vacuo and the resulting residue was partitioned between H2O and CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a light yellow oil. were heated The reaction mixture was then cooled in ice the completion of addition The volatiles were then removed in vacuo the resulting residue was partitioned between H2O and CH2Cl2 The organic layer was separated washed with brine dried over MgSO4 filtered

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

Procedure: A mixture of 2,3-dimethylbenzaldehyde (1 eq.), cyclopropylamine (1.2 eq.) and sodium bicarbonate (1.5 eq.) were heated at reflux in MeOH (0.5 M) for 1 h. The reaction mixture was then cooled in ice and sodium borohydride (1.2 eq.) was introduced portionwise. Following the completion of addition, the reaction mixture was warmed to RT and stirred at RT for 1 h. The volatiles were then removed in vacuo and the resulting residue was partitioned between H2O and CH2Cl2. The organic layer was separated, washed with brine, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a light yellow oil. were heated The reaction mixture was then cooled in ice the completion of addition The volatiles were then removed in vacuo the resulting residue was partitioned between H2O and CH2Cl2 The organic layer was separated washed with brine dried over MgSO4 filtered

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

Procedure: Synthesized according to typical procedures H and E from bicyclononene BN10 and cyclopropyl-(2,3dimethylbenzyl)amine. LC-MS: Rt=0.91; ES+: 632.31. Synthesized

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

Procedure: Synthesized according to typical procedure J from 2,3-dimethylbenzaldehyde and cyclopropylamine. Synthesized

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: Synthesized according to typical procedures H and E from bicyclononene BN10 and cyclopropyl-(2,3dimethylbenzyl)amine. LC-MS: Rt=0.91; ES+: 632.31. Synthesized