Ethyl Acetate → N-(2,2-Diethoxyethyl)-5-phenethyloxy-pentan-1-amine
Reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH2:21])[CH3:17].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>C(O)C>[CH2:16]([O:18][CH:19]([O:22][CH2:23][CH3:24])[CH2:20][NH:21][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:17]Participants
6
Conditions
- Temperature
- 78 °C
Procedure
2-(5-Bromopentoxy)ethylbenzene (1.5 g) was dissolved in ethanol (30 mL) and treated with 2,2-diethoxyethylamine (0.86 g) and diisopropylethylamine (1.8 mL) at room temperature. The reaction was stirred at 78° C. for 48 hours and was then poured into ethyl acetate (10 mL), washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give the sub-titled compound (0.2 g) as an oil.
Workup
- washwashed with water (10 mL) and brine (10 mL)
- dry with materialThe organic layer was dried over anhydrous magnesium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-51f5bc0719ef414f8a7f7a946f96090f
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709511B2
Reaction notes
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