Hydrochloric Acid → 1-[2-Chloro-4-(2-diethylaminoethoxy)phenyl]-2-methylene-1-butanone
Reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])[CH:5]=[CH:4][C:3]=1[C:16](=[O:20])[CH2:17][CH2:18][CH3:19].Cl.[CH3:22]NC.C=O.Cl>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])[CH:5]=[CH:4][C:3]=1[C:16](=[O:20])[C:17](=[CH2:22])[CH2:18][CH3:19]Participants
5
Procedure
A mixture of 8.9 g. (0.03 mole) of 1-[2-chloro-4-(2-diethylaminoethoxy)phenyl]-1-butanone, 2.7 g. (0.033 mole) of dimethylamine hydrochloride, 1.8 g. (0.06 mole) of paraformaldehyde and 5 ml. of concentrated hydrochloric acid is heated on the steam bath for 2 hours. The mixture is digested on the steam bath with 700 ml. of water, filtered and the filtrate added to 350 ml. of 10% aqueous sodium bicarbonate. The solution is heated on the steam bath for 1 hr., cooled and extracted with ether. The ether extract is washed with water, dried over sodium sulfate, filtered and evaporated to dryness on the steam bath. The product is obtained upon distillation in vacuo (0.3 mm.) as a pale yellow oil.
Workup
- additionA mixture of 8.9 g
- filtrationof water, filtered
- additionthe filtrate added to 350 ml
- temperatureThe solution is heated on the steam bath for 1 hr
- temperature, cooled
- extractionextracted with ether
- extractionThe ether extract
- washis washed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness on the steam bath
- customThe product is obtained upon distillation in vacuo (0.3 mm.) as a pale yellow oil
Sources & evidence
- ORD record
- ord-6e08bfd85b414c0a80e7a060c673ec61
- Source dataset
- uspto-grants-1983_06
- Patent number
- US04390537
Reaction notes
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