Ammonium Chloride → HCID 13882441, compound

HRID 1583317Notes

Reaction equation

HRID 1583317 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]2[CH2:27][CH3:28])=[CH:13][CH:12]=1)=[O:10].[Cl-].[NH4+]>CCOCC>[CH2:27]([CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][N:21]1[CH2:20][CH2:19][CH2:18][O:17][C:14]1[CH:13]=[CH:12][C:11]([C:9]([C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[O:6][CH3:5])([OH:10])[CH2:1][CH3:2])=[CH:16][CH:15]=1)[CH3:28]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 20260685HCID 20260685, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 13882441HCID 13882441, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 80 ml. of a 2.5 molar ethereal ethyl magnesium bromide solution a solution of 19.1 g. of 2-methoxy-4'-[3-(2-ethyl-piperid-1-yl)-propoxy]-benzophenone in 150 ml. of ether is added dropwise, with stirring at a temperature between 0° C. and 5° C., whereupon the reaction mixture is slightly boiled for one hour. After cooling the mixture is decomposed with a 10% aqueous ammonium chloride solution, and the aqueous phase is extracted with ether. The organic phase is washed to neutral with water, dried over anhydrous magnesium sulfate, and ether is distilled off under reduced pressure. Fractionation of the residue in vacuum yields 14.6 g. of the named compound, boiling at 224° to 226° C./13.3 Pa.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionthe aqueous phase is extracted with ether
  3. washThe organic phase is washed to neutral with water
  4. dry with materialdried over anhydrous magnesium sulfate, and ether
  5. distillationis distilled off under reduced pressure
  6. customFractionation of the residue in vacuum yields 14.6 g

Sources & evidence

ORD record
ord-09764e116cac4901bc36a78669e757a4
Source dataset
uspto-grants-1985_11
Patent number
US04551465

Reaction notes

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