Chloride → HCID 131723344, compound
Reaction equation
[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1=[O:11])[CH3:3].[CH:18]1([Mg][Cl:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Cl-]>O1CCCC1>[ClH:25].[CH3:3][N:2]([CH:4]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][C:6]1([OH:11])[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH3:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3.0 g (13.0 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanone prepared according to Example 1 were dissolved in 10 ml of tetrahydrofuran, added dropwise while cooling in an ice bath to 7.8 ml (15.6 mmole) of cyclohexylmagnesium chloride (2 M solution in tetrahydrofuran), and stirred for 15 hours at RT. The reaction mixture was worked up by adding 20 ml of saturated ammoniun chloride solution while cooling in an ice bath and extracted three times at RT, with 20 ml of ether each time. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator (500 to 10 mbar). 4.03 g of crude base (98.5% of theory) were obtained, from which 2.22 g of 2-(dimethylaminophenylmethyl)bicyclohexyl-1-ol, hydrochloride (48.5% of theory) with a melting point of 220° C.-223° C. were obtained according to the procedure described in Example 1 (3rd Stage) with chlorotrimethylsilane/water in 2-butanone.
Workup
- additionadded dropwise
- temperaturewhile cooling in an ice bath
- extractionextracted three times at RT
- dry with materialThe combined organic extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated by evaporation on a rotary evaporator (500 to 10 mbar)
Sources & evidence
- ORD record
- ord-8dcf814bdedf4b8f97b7483fe70fb27f
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410790B1
Reaction notes
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