反応 #350565

反応方程式

HCl

Ethyl pipecolinate

trimethylaluminum

product

4-Chloro-2-fluoro-5-(1 -methylethoxy)aniline

→

title compound

N-[4-Chloro-2-fluoro-5-(1 -methylethoxy)phenyl]piperidine-2-carboxamide

溶媒

methylene chloride

H2O

CH2Cl2

反応条件

後処理

1. 1
   その他The aqueous layer was separated
2. 2
   workup.ADDITION500 mL of CH2Cl2 was added
3. 3
   その他The organic layer was separated
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated to dryness under vacuum

実験手順

The product of Example 1, Step A (4.25 g, 26.37 mmol) was dissolved in CH2Cl2 (200 mL). A solution of 2.0M trimethylaluminum (52.75 mmol) was added dropwise under nitrogen at 0° C. The resultant mixture was stirred at room temperature overnight. Ethyl pipecolinate (4.15 g) was added dropwise to the mixture and the mixture was stirred for 2 days. To the reaction mixture 6N HCl (100 mL) was added dropwise at 0° C. 200 mL of H2O was added, followed by the addition of 150 mL of methylene chloride. The aqueous layer was separated and basicified to pH 10 with 50% aqueous NaOH. 500 mL of CH2Cl2 was added. The organic layer was separated, dried over MgSO4, filtered and evaporated to dryness under vacuum to give the title compound of Step A as a white solid, 4.7 g. m.p. 96°-98° C. 1H NMR (CDCl3): δ9.25 (br s,1H), 8.17 (d,1H), 7.13 (d,1H) 4.58 (m,1H), 3.20 (M,1H), 3.10 (m,1H), 2.79 (m,1H), 2.00 (m,1H), 1.89 (m,2H), 1.60-1.40 (m,4H), 1.36 (d,6H).

出典