Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH2:8][CH2:7][CH2:6]2.Cl.[CH3:15][CH:16]1[O:21][CH:20]([CH3:22])[CH2:19][NH:18][CH2:17]1.[CH2:23]=O.O>C(O)C.Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[CH:8]([CH2:23][N:18]1[CH2:19][CH:20]([CH3:22])[O:21][CH:16]([CH3:15])[CH2:17]1)[CH2:7][CH2:6]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one (17.6 g, 0.1 mol), 2,6-dimethylmorpholine hydrochloride (15.1 g, 0.1 mol), and paraformaldehyde (6.0 g, 0.2 mol) were refluxed together in ethanol (50 ml) with concentrated hydrochloric acid (0.25 ml) as a catalyst for 3 hours. The reaction was cooled and poured into water containing concentrated hydrochloric acid (5 ml) and extracted with ether (200 ml). The aqueous solution was cooled in ice and neutralised with sodium hydroxide solution (10%) then extracted with ether (2×200 ml) dried over magnesium sulphate and evaporated under reduced pressure to give a residue which was recrystallised from petrol (60°-80°) to give 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one a white crystalline solid (10 g, 33% yield) melting at 110° C.
Workup
- temperatureThe reaction was cooled
- extractionextracted with ether (200 ml)
- temperatureThe aqueous solution was cooled in ice and neutralised with sodium hydroxide solution (10%)
- extractionthen extracted with ether (2×200 ml)
- dry with materialdried over magnesium sulphate
- customevaporated under reduced pressure
- customto give a residue which
- customwas recrystallised from petrol (60°-80°)
Sources & evidence
- ORD record
- ord-b4e037832f3844949cd1d2460ced76f7
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04785006
Linked notes
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