2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol synthesis
- Product Name:2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
- CAS Number:2914-77-4
- Molecular formula:C16H25NO2
- Molecular Weight:263.38
![Cyclohexanone, 2-[(dimethylamino)methyl]-, (+)- (9CI)](/CAS/GIF/769092-24-2.gif)
Yield:-
Reaction Conditions:
Stage #1: 3-methoxyphenyl bromidewith toluene-4-sulfonic acid in tetrahydrofuran at -60; for 0.75 h;
Stage #2: 2-((dimethylamino)methyl)cyclohexan-1-one in tetrahydrofuran; for 1.5 h;
Steps:
1.1; 2.1 Example 1
(1) Compound I (3.70g, 20mmol) was dissolved in anhydrous THF (30ml), cooled to -60°C, and then 2.5M n-butyllithium tetrahydrofuran solution (8.0ml, 20mmol) was slowly added dropwise. The reaction was carried out at this temperature for 45 min; then, a THF solution (10 ml) of 2-(N,N-dimethylaminomethyl)cyclohexanone (3.5 g, 22 mmol) was slowly added dropwise, and the dropwise addition was completed, and the reaction was continued for 1.5 h. Saturated ammonium chloride aqueous solution (5ml) was added to quench the reaction, the reaction solution was concentrated, water (100ml) and DCM (100ml×3) were added to the residue for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated to obtain the compound II, directly used in the next reaction without purification.
References:
CN114292199,2022,A Location in patent:Paragraph 0005; 0011
