Diethyl Ether → 2-(N-Benzylmethylamino)-methyl-1-(3-methoxybenzyl)cyclohexanol

HRID 1156515Notes

Reaction equation

HRID 1156515 reaction equation
Cl.[CH2:2]([CH2:9][NH:10][C:11]1([CH3:17])[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Cl.[Mg].[Cl-].[NH4+].[CH3:31]COCC>>[CH2:2]([CH2:9][NH:10][C:11]1([CH3:17])[CH2:15][CH2:14][CH2:13][CH2:31][C:12]1([CH2:23][C:22]1[CH:25]=[CH:26][CH:27]=[C:20]([O:19][CH3:18])[CH:21]=1)[OH:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 699943-Methoxybenzyl chlorideHCID 5462224MagnesiumHCID 205348202-(N-Benzylmethylamino)-methyl-cyclopentanone hydrochloride

Product 1

HCID 205348182-(N-Benzylmethylamino)-methyl-1-(3-methoxybenzyl)cyclohexanol

Procedure

67 g (0.25 mole) of 2-(N-benzylmethylamino)methylcyclohexanone hydrochloride obtained as described in (a) are introduced in the course of 30 minutes, whilst stirring and cooling, into a Grignard solution which has been prepared from 110 g (0.7 mole) of 3-methoxybenzyl chloride, 16.8 g of magnesium and 700 ml of dry ether; stirring is continued for 16 hours at room temperature, the reaction mixture is decomposed with an excess of concentrated ammonium chloride solution, the ether layer is separated off and dried with sodium sulfate, the ether is driven off and the residue is distilled under reduced pressure.

Workup

  1. additionare introduced in the course of 30 minutes
  2. temperaturecooling, into a Grignard solution which
  3. stirringstirring
  4. customthe ether layer is separated off
  5. dry with materialdried with sodium sulfate
  6. distillationthe residue is distilled under reduced pressure

Sources & evidence

ORD record
ord-8c5ce06aa4964f2aa00319102a5e8b47
Source dataset
uspto-grants-1982_06
Patent number
US04336263

Reaction notes

Loading…