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Ammonium Chloride → 3-Chloro-4'-[2-(diethylamino)-ethoxy]-alpha-ethyl-benzhydrol

HRID 364650
Notes
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Reaction equation

HRID 364650 reaction equation
[CH2:1]([Li])[CH3:2].[Cl:4][C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:12][CH:11]=1)=[O:9].[Cl-].[NH4+]>CCOCC>[Cl:4][C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[C:8]([CH2:1][CH3:2])([OH:9])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][N:19]([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:14][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 202395683-Chloro-4'-[2-(diethylamino)-ethoxy]-benzophenoneHCID 178506846HCID 178506846, compound

Product 1

HCID 202395593-Chloro-4'-[2-(diethylamino)-ethoxy]-alpha-ethyl-benzhydrol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 125 ml. of a 0.8 molar ethereal ethyl lithium solution a solution of 13.3 g. of 3-chloro-4'-[2-(diethylamino)-ethoxy]-benzophenone in 160 ml. of ether is added dropwise, with stirring under argon atmosphere, at a temperature between -20° C. and -15° C. The reaction mixture is then stirred at room temperature for one hour, and is decomposed with a saturated aqueous ammonium chloride solution, under cooling. The aqueous phase is extracted with ether, the ethereal phases are combined and washed to neutral with water. After drying over anhydrous magnesium sulfate, ether is distilled off under reduced pressure. Crystallization of the solid residue from n-hexane yields 8.9 g. of the title compound, melting at 64° to 65° C.

Workup

  1. stirringThe reaction mixture is then stirred at room temperature for one hour
  2. temperatureunder cooling
  3. extractionThe aqueous phase is extracted with ether
  4. washwashed to neutral with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate, ether
  6. distillationis distilled off under reduced pressure
  7. customCrystallization of the solid residue from n-hexane
  8. customyields 8.9 g

Sources & evidence

ORD record
ord-fc4d06e26eda4476b08a3f37189dff98
Source dataset
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04605672

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes