1(2H)-Naphthalenone, 3,4-dihydro-2-((dimethylamino)methyl)- → (1RS,2RS)-2-Dimethylaminomethyl-1-(3-methoxybenzyl)-1,2,3,4-tetrahydro-naphth-1-ol

HRID 2181279Notes

Reaction equation

HRID 2181279 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=[O:15])[CH3:3].[Mg].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH2:22]Cl.[Cl-].[NH4+]>C(OCC)C>[CH3:3][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([CH2:22][C:21]1[CH:24]=[CH:25][CH:26]=[C:19]([O:18][CH3:17])[CH:20]=1)[OH:15])[CH3:1]

Participants

6

Reactant 4

HCID 238121(2H)-Naphthalenone, 3,4-dihydro-2-((dimethylamino)methyl)-HCID 25517Ammonium ChlorideHCID 699943-Methoxybenzyl chlorideHCID 5462224Magnesium

Product 1

HCID 12043464(1RS,2RS)-2-Dimethylaminomethyl-1-(3-methoxybenzyl)-1,2,3,4-tetrahydro-naphth-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 8.13 g 2-dimethylaminomethyl-3,4-dihydro-naphthalen-1-one in 20 ml dry diethyl ether was added dropwise to a freshly prepared Grignard reagent of 1.46 g magnesium filings and 8.8 ml 3-methoxybenzyl chloride in 50 ml dry diethyl ether at 20° C., while stirring. The reaction mixture was heated under reflux for 3 hours, decomposed by dropwise addition of 30 ml of a saturated ammonium chloride solution and, after dilution with distilled water, extracted three times with 50 ml diethyl ether each time. The extracts were washed with a saturated sodium chloride solution, dried over sodium sulfate and evaporated in vacuo. The oily residue was purified by column chromatography with ethyl acetate/methanol=20/1 as the eluting agent. 9.41 g (72.3% of th.) of the title compound were obtained here as a diastereomer mixture.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionafter dilution with distilled water, extracted three times with 50 ml diethyl ether each time
  4. washThe extracts were washed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe oily residue was purified by column chromatography with ethyl acetate/methanol=20/1 as the eluting agent

Sources & evidence

ORD record
ord-1ca96c81f7e24e9688e9ba634311fa83
Source dataset
uspto-grants-2005_05
Patent number
US06890952B2

Reaction notes

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