Water → HCID 18670147, compound

HRID 1059338Notes

Reaction equation

HRID 1059338 reaction equation
[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[O:11][CH3:12].C([Li])CCC.[CH2:20]([N:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CCOCC.CCCCCC>[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:9]=[CH:8][C:7]([C:30]2([OH:33])[CH2:31][CH2:32][N:27]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:28][CH2:29]2)=[CH:6][C:5]=1[O:11][CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 192201-Benzyl-4-piperidoneHCID 18670342HCID 18670342, compoundHCID 178418339Butyllithium

Product 1

HCID 18670147HCID 18670147, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

15.0 g of 4-bromo-2-methoxybenzaldehyde dimethyl acetal was dissolved in 150 ml of ether and the obtained solution was cooled to −50° C. Then 25.3 ml of a 1.6 M solution of n-butyllithium in hexane was dropped thereinto. 1 hour thereafter, 30 ml of a solution of 11.7 ml of 1-benzyl-4-piperidone in diethyl ether was dropped thereinto in such a manner that the bulk temperature did not exceed −35° C. After stirring at room temperature for 50 minutes, water was added thereto followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 23.82 g of a pale yellow oily substance was obtained. 13.82 g of this oily substance was purified by silica gel column chromatography (eluted with dichloromethane/methanol) to thereby give 6.31 g of the title compound as a pale yellow solid.

Workup

  1. customdid not exceed −35° C
  2. extractionthereto followed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  5. distillationAfter distilling off the solvent under reduced pressure, 23.82 g of a pale yellow oily substance
  6. customwas obtained
  7. custom13.82 g of this oily substance was purified by silica gel column chromatography (eluted with dichloromethane/methanol)

Sources & evidence

ORD record
ord-6fe9e1d442924a35a0225fd54f400a56
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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