Ammonia → HCID 66939016, compound

Participants

Reaction Conditions

Reaction Steps

Combine 1-methyl-4-(3-aminophenylamino)piperidine triacetate (Preparation 18, 460 mg, 1.17 mmol) and CH2Cl2 (13 mL); stir and cool to 0° C. Add isovaleryl chloride (135 μL, 1.05 mmol), and stir at room temperature for 18 hr. Load onto a 5 g SCX cartridge (mega bond elut, Varian). Wash resin with methanol, then elute product with 2 M ammonia in methanol. Concentrate in vacuo, and chromatograph on silica gel, eluting with a gradient of 1–15% (2M ammonia in methanol) in CH2Cl2. Concentrate in vacuo. Dissolve the purified oil (115 mg, 38% isolated yield) in methanol, add solid NH4Cl (21.2 mg, 1 eq) and sonicate the solution at room temperature for 15 min. Concentrate in vacuo to provide the title compound: mass spectrum (ion spray): m/z=290.2 (M+1); Anal calc'd for C17H28ClN3O.0.1H2O: Theory: C, 62.31; H, 8.67; N, 12.82. Found: C, 62.32; H, 8.78; N, 12.56.

Provenance & Evidence