反应详情

A standard setup was used with a N2 inlet. Initially, the amine 105 (2.42 g, 14.38 mmol) in H2CCl2 (35 ml) was added followed by NaOH (10%, 14.42 g, 35.95 mmol) which resulted in a heterogenous mixture. To this mixture was added 4-nitrophenylacetyl chloride (3,16 g, 15.82 mmol) dropwise over a 15-min period. Stirring was continued for an additional 3 h upon which the brown mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was extracted (H2CCl2, 3×25 ml), and the organic layers were combined. After drying (Na2SO4, 2 h), the organic solution was filtered and concentrated to give 94 as a light brown solid (3.3 g, 69.2 %); mp 93°-94°]C. IR (KBr) 3090 (Ar-H), 2960, 2920, 2800, 2740 (C-H), 1625 (NC=O) cm-1 ; 1H NMR (DCCl3) d 0.94 (dd, 6 H, CH3 isopropyl), 1.69 [q, 2 H, H(9)], 1.92 [bs, 2 H, H(1,5)], 2.46 [m, 3H, ring protons, C-H, isopropyl), 2.79 (d, 1 H, ring proton), 2.93 (td, 2 H, ring protons), 3.39 (d, 1 H, ring proton), 3.79 (s, 2 H, CH2 -Ar), 3.84 (d, 1 H, ring proton), 4.57 (d, 1 H, ring proton), 7.44 (d, 2 H; Ar-H), 8.15 (d, 2 H, Ar-H); 13C NMR (DCCl3) ppm 16.83, 18.44 (CH3 isopropyl), 28.76, 29.42 [C(1,5)1, 31.57 [C(9)], 40.62 (CH2 -Ar), 46.76 (C-H isopropyl), 50.60, 52.78, 54.03, 54.42 [C(2,4,6,8)], 123.37, 130.02, 143.58, 146.56 (Ar-C), 167.93 (NC=O). Amide 94 was used without further purification.

1. customA standard setup was used with a N2 inlet
2. customresulted in a heterogenous mixture
3. customthe brown mixture was transferred to a separatory funnel
4. customthe layers were separated
5. extractionThe aqueous layer was extracted (H2CCl2, 3×25 ml)
6. dry with materialAfter drying (Na2SO4, 2 h)
7. filtrationthe organic solution was filtered
8. concentrationconcentrated