N-[2-[(4-chlorophenyl)methylamino]ethyl]acetamide

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(2-amino-ethyl)-acetamide (1.2 eq.) in MeOH were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1) to afford N-[2-(4-chloro-benzylamino)-ethyl]-acetamide. The reaction was refluxed for 4 h 15 h at 20° C The crude was concentrated under reduced pressure then partitioned between water and DCM The aqueous layer was then extracted twice with DCM dried over MgSO4 filtered concentrated under reduced pressure The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(2-amino-ethyl)-acetamide (1.2 eq.) in MeOH were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1) to afford N-[2-(4-chloro-benzylamino)-ethyl]-acetamide. The reaction was refluxed for 4 h 15 h at 20° C The crude was concentrated under reduced pressure then partitioned between water and DCM The aqueous layer was then extracted twice with DCM dried over MgSO4 filtered concentrated under reduced pressure The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of N-(2-amino-ethyl)-acetamide (1.2 eq.) in MeOH were added NaHCO3 (1.5 eq.) and 4-chlorobenzaldehyde (1 eq.). The reaction was refluxed for 4 h, then cooled to 0° C. NaBH4 (1.2 eq.) was added portionwise. The reaction was stirred for 1 h at 0° C., then 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and DCM. The aqueous layer was then extracted twice with DCM. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1) to afford N-[2-(4-chloro-benzylamino)-ethyl]-acetamide. The reaction was refluxed for 4 h 15 h at 20° C The crude was concentrated under reduced pressure then partitioned between water and DCM The aqueous layer was then extracted twice with DCM dried over MgSO4 filtered concentrated under reduced pressure The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 1/0 to 0/1)