Reaction equation
[CH2:1]([NH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:2].C(N(C(C)C)CC)(C)C.Br[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>>[CH2:1]([N:3]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH3:2]Participants
Procedure
N-Ethyl-1-naphthylamine 8 (11.4 gm, 0.066 moles), diisopropylethylamine (11.2 gm, 0.087 moles), and ethyl 4-bromobutyrate (19 gm, 0.097 moles) were heated at 110-120° C. for 16 hours under argon at which time, HPLC indicated the reaction was complete. The mixture solidified upon cooling to room temperature. The solid was partitioned between DCM and water. The aqueous layer was extracted with two portions of DCM. The combined organic extracts were washed with saturated NaCl, dried over MgSO4, filtered, concentrated under reduced pressure by rotary evaporation to give 22 gm of a crude solid. The solid was purified by flash chromatography, eluting with ethyl acetate and hexane, to give ethyl 4-(ethylnaphthylamino)butanoate 9 (6.04 gm, 32% yield) as an orange oil. 1H NMR (CDCl3) δ 8.3, 1H, m; 7.8, 1H, m; 7.35-7.55, 4H, m; 7.15, 1H, m; 4.05, 2H, q; 3.18, 4H, m; 2.32, 2H, t; 1.8, 2H, m; 1.20, 3H, t; 1.05, 3H, t.
Workup
- customThe solid was partitioned between DCM and water
- extractionThe aqueous layer was extracted with two portions of DCM
- washThe combined organic extracts were washed with saturated NaCl
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure by rotary evaporation
- customto give 22 gm of a crude solid
- customThe solid was purified by flash chromatography
- washeluting with ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-cff845f92809466c8021c91a15ca99d8
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637658B2
Linked notes
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