N-methoxy-N-methylheptanamide

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: n-Butyllithium (2.5 M in hexanes, 51 mL, 127 mmol) was added dropwise to 4-bromo-N,N-dimethylaniline (23.1 g, 115 mmol, Aldrich Chemical Co.) in anhydrous THF at -78° C. After 10 min. a solution of N-methyl-N-methoxyheptanamide (10.0 g, 57.7 mmol) in 20 mL THF was added dropwise via canula. The reaction was allowed to proceed 1 hr., then quenched with 1 N aq. HCl and carefully poured into sat. NaHCO3. The aqueous layer was extracted with ethyl ether, and the combined organic fraction was washed with water, brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (15% EtOAc/hexanes) yielded 1-(4-dimethylaminophenyl)heptan-1-one as a yellow solid (6.49 g, 48%). MS 234 (M+H)+. , then quenched with 1 N aq. HCl carefully poured into sat. NaHCO3 The aqueous layer was extracted with ethyl ether the combined organic fraction was washed with water, brine dried (MgSO4) concentrated in vacuo

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

Procedure: Triethylamine (19.6 g, 194 mmol) was added dropwise to a suspension of N,O-dimethylhydroxylamine hydrochloride (6.93 g, 71 mmol) in anhydrous CH2Cl2 at 0° C. Heptanoylchloride (9.60 g, 65 mmol) was then added dropwise and the reaction was stirred 1 hour. The crude product mixture was poured into water and the separated aqueous phase was extracted with CH2Cl2. The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10 g (89%) N-methyl-N-methoxyheptanamide as a yellow oil. the separated aqueous phase was extracted with CH2Cl2 The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine dried (Na2SO4) concentrated in vacuo

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

Procedure: n-Butyllithium (2.5 M in hexanes, 51 mL, 127 mmol) was added dropwise to 4-bromo-N,N-dimethylaniline (23.1 g, 115 mmol, Aldrich Chemical Co.) in anhydrous THF at -78° C. After 10 min. a solution of N-methyl-N-methoxyheptanamide (10.0 g, 57.7 mmol) in 20 mL THF was added dropwise via canula. The reaction was allowed to proceed 1 hr., then quenched with 1 N aq. HCl and carefully poured into sat. NaHCO3. The aqueous layer was extracted with ethyl ether, and the combined organic fraction was washed with water, brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (15% EtOAc/hexanes) yielded 1-(4-dimethylaminophenyl)heptan-1-one as a yellow solid (6.49 g, 48%). MS 234 (M+H)+. , then quenched with 1 N aq. HCl carefully poured into sat. NaHCO3 The aqueous layer was extracted with ethyl ether the combined organic fraction was washed with water, brine dried (MgSO4) concentrated in vacuo

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

Procedure: Triethylamine (19.6 g, 194 mmol) was added dropwise to a suspension of N,O-dimethylhydroxylamine hydrochloride (6.93 g, 71 mmol) in anhydrous CH2Cl2 at 0° C. Heptanoylchloride (9.60 g, 65 mmol) was then added dropwise and the reaction was stirred 1 hour. The crude product mixture was poured into water and the separated aqueous phase was extracted with CH2Cl2. The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10 g (89%) N-methyl-N-methoxyheptanamide as a yellow oil. the separated aqueous phase was extracted with CH2Cl2 The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine dried (Na2SO4) concentrated in vacuo

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

Procedure: n-Butyllithium (2.5 M in hexanes, 51 mL, 127 mmol) was added dropwise to 4-bromo-N,N-dimethylaniline (23.1 g, 115 mmol, Aldrich Chemical Co.) in anhydrous THF at -78° C. After 10 min. a solution of N-methyl-N-methoxyheptanamide (10.0 g, 57.7 mmol) in 20 mL THF was added dropwise via canula. The reaction was allowed to proceed 1 hr., then quenched with 1 N aq. HCl and carefully poured into sat. NaHCO3. The aqueous layer was extracted with ethyl ether, and the combined organic fraction was washed with water, brine, dried (MgSO4), and concentrated in vacuo. Flash chromatography (15% EtOAc/hexanes) yielded 1-(4-dimethylaminophenyl)heptan-1-one as a yellow solid (6.49 g, 48%). MS 234 (M+H)+. , then quenched with 1 N aq. HCl carefully poured into sat. NaHCO3 The aqueous layer was extracted with ethyl ether the combined organic fraction was washed with water, brine dried (MgSO4) concentrated in vacuo

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

Procedure: Triethylamine (19.6 g, 194 mmol) was added dropwise to a suspension of N,O-dimethylhydroxylamine hydrochloride (6.93 g, 71 mmol) in anhydrous CH2Cl2 at 0° C. Heptanoylchloride (9.60 g, 65 mmol) was then added dropwise and the reaction was stirred 1 hour. The crude product mixture was poured into water and the separated aqueous phase was extracted with CH2Cl2. The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10 g (89%) N-methyl-N-methoxyheptanamide as a yellow oil. the separated aqueous phase was extracted with CH2Cl2 The combined organic layers was washed with aq. HCl, sat. NaHCO3, brine dried (Na2SO4) concentrated in vacuo