Ethyl 4-bromobutyrate → HCID 67431209, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][NH2:11].Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C(N(C(C)C)CC)(C)C>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]Participants
Procedure
(2,5-Dimethylphenyl)ethylamine 18 (5.36 gm, 0.036 moles), ethyl 4-bromobutyrate (9.11 gm, 0.046 moles) and diisopropylethylamine (6.07 gm, 0.047 moles) were heated at 110-120° C. overnight, cooled, and partitioned between 100 ml DCM and 100 ml water. The aqueous layer was extracted twice with 50 ml portions of DCM. The combined organic extracts were washed with saturated NaCl, dried over Na2SO4, filtered, and concentrated by rotary evaporation under reduced pressure. The crude product was purified by flash chromatography on silica gel, eluting with a gradient mixture of methanol and DCM. Ethyl 4-[(2,5-dimethylphenyl)ethylamino]butanoate 19 (4.66 gm, 49% yield) was isolated as a slightly yellow oil after removing the solvent. 1H NMR (CDCl3) δ 7.07, 1H, d; 6.88, 1H, br s; 6.79, 1H, d; 4.10, 2H, q; 2.9, 4H, m; 2.35, 2H, t; 2.29, 3H, s; 2.24, 3H, s; 1.74, 2H, m; 1.24, 3H, t; 0.98, 3H, t.
Workup
- temperaturecooled
- custompartitioned between 100 ml DCM and 100 ml water
- extractionThe aqueous layer was extracted twice with 50 ml portions of DCM
- washThe combined organic extracts were washed with saturated NaCl
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated by rotary evaporation under reduced pressure
- customThe crude product was purified by flash chromatography on silica gel
- washeluting with a gradient mixture of methanol and DCM
Sources & evidence
- ORD record
- ord-8fc2c0504d4d4e4ebf6eaac17f53ea1c
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637658B2
Reaction notes
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