Formaldehyde → HCID 13676511, compound
Reaction equation
[Cl-].[CH3:2][NH2+:3][CH3:4].C=O.C(O[C:11](=[O:13])[CH3:12])(=O)C.[C:14]([NH:17][C:18]1[CH:19]=[C:20]2C(=[CH:26][CH:27]=1)[C:24](=O)[CH2:23][CH2:22][CH2:21]2)(=[O:16])[CH3:15].[OH-].[Na+]>Cl.O.CC(C)=O>[C:14]([NH:17][C:18]1[CH:19]=[C:20]2[C:12](=[CH:26][CH:27]=1)[C:11](=[O:13])[CH:23]([CH2:24][N:3]([CH3:4])[CH3:2])[CH2:22][CH2:21]2)(=[O:16])[CH3:15]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 100 °C
Procedure
Dimethylammonium chloride (2.34 g), formalin solution (1.58 g;37%) and concentrated hydrochloric acid (1 drop) was stirred at room temperature for 5 minutes then added to acetic anhydride (11.4 ml ). After about 20 minutes vigorous boiling occurred. 6-Acetamido-1-tetralone (3.6 g) was then added and the mixture was stirred at 100° C. for one hour. Evaporation of the reaction mixture under reduced pressure yielded an orange solid which was treated with acetone (15 ml ) for 3 minutes. The residue obtained on removal of acetone was dissolved in water (20 ml ) and treated with 2N sodium hydroxide to give pH 10. The precipitated oil was extracted with dichloromethane, dried (MgSO4) and evaporated to give crude 6-acetamido-2-dimethylaminomethyl-1-tetralone (5.0 g;M+ =260) which was taken up in acetone (30 ml ) and treated with iodomethane (12 ml ). The precipitate obtained was filtered off and washed with ether to give 6-acetamido-1-oxo-1,2,3,4-tetrahydro-2-naphthyl-trimethyl ammonium iodide (4.25 g; m.p. 168°-70°).
Workup
- customEvaporation of the reaction mixture under reduced pressure
- customyielded an orange solid which
- customto give pH 10
- extractionThe precipitated oil was extracted with dichloromethane
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-a5bde6f0d99641b5938b720ce2235fd9
- Source dataset
- uspto-grants-1988_07
- Patent number
- US04755511
Reaction notes
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