Potassium Carbonate → e-(2Rs)-[1-(2-methoxybenzylidene)-1,2,3,4-tetrahydro-naphth-2-ylmethyl]-dimethylamine hydrochloride

HRID 2181280Notes

Reaction equation

HRID 2181280 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:23][CH3:24])O)[CH3:3].COC1C=CC=CC=1C[Cl:30].CN(CC1CCC2C(=CC=CC=2)C1=O)C.C(=O)([O-])[O-].[K+].[K+].C[Si](C)(C)Cl.O>C(O)=O.O.CC(=O)CC>[ClH:30].[CH3:24][O:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1/[CH:16]=[C:6]1\[CH:5]([CH2:4][N:2]([CH3:3])[CH3:1])[CH2:14][CH2:13][C:12]2[C:7]\1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 238121(2H)-Naphthalenone, 3,4-dihydro-2-((dimethylamino)methyl)-HCID 814952-(Chloromethyl)anisoleHCID 22485733(1RS,2RS)-2-dimethylaminomethyl-1-(2-methoxy-benzyl)-1,2,3,4-tetrahydronaphth-1-olHCID 86753056Chlorotrimethylsilane water

Product 1

HCID 22485749e-(2Rs)-[1-(2-methoxybenzylidene)-1,2,3,4-tetrahydro-naphth-2-ylmethyl]-dimethylamine hydrochloride

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 7.06 g (1RS,2RS)-2-dimethylaminomethyl-1-(2-methoxy-benzyl)-1,2,3,4-tetrahydronaphth-1-ol (prepared analogously to example 1, stage 1 from 2-methoxybenzyl chloride and 2-dimethylaminomethyl-3,4-dihydronaphthalen-1-one) in 45 ml formic acid was stirred at 20° C. for 3 hours. It was diluted with 100 ml water and rendered alkaline by addition of potassium carbonate in portions up to pH 9. The mixture was extracted three times with 50 ml methylene chloride each time. The extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The residue was separated by column chromatography with ethyl acetate as the eluting agent, the two title compounds being obtained as bases, which were converted into the hydrochlorides with trimethylchlorosilane/water in 2-butanone.

Workup

  1. extractionThe mixture was extracted three times with 50 ml methylene chloride each time
  2. washThe extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was separated by column chromatography with ethyl acetate as the eluting agent
  6. customthe two title compounds being obtained as bases, which

Sources & evidence

ORD record
ord-0f0511d3cd684d45923ba9dd144f299b
Source dataset
uspto-grants-2005_05
Patent number
US06890952B2

Reaction notes

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