Water → (betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamine

HRID 1771019Notes

Reaction equation

HRID 1771019 reaction equation
Cl[CH2:2][C@H:3]([CH3:21])[C@H:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[CH2:5][CH3:6].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:29][NH:30][CH3:31].O>CN(C)C=O>[CH2:5]([C@@H:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=1)[C@@H:3]([CH3:21])[CH2:2][N:30]([CH3:31])[CH3:29])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 601648431-[(1R,2R)-3-chloro-1-ethyl-2-methylpropyl]-3-(phenylmethoxy)benzene

Product 1

HCID 60164845(betaR,gammaR)-gamma-ethyl-N,N,beta-trimethyl-3-(phenylmethoxy)benzenepropanamineYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 42 (2.4 g, 8 mmol) was dissolved in N,N-dimethylformamide, potassium carbonate (2.7 g, 20 mmol) and dimethylamine hydrochloride (0.7 g, 8 mmol) were added therein, then it was reacted at room temperature for 12 hours. After that, the reaction solution was poured into water, the aqueous phase was extracted with dichloromethane twice, then the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, concentrated, and separated through silica gel column chromatography to give target 2.2 g, yield: 90%.

Workup

  1. customit was reacted at room temperature for 12 hours
  2. extractionthe aqueous phase was extracted with dichloromethane twice
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customseparated through silica gel column chromatography
  7. customto give

Sources & evidence

ORD record
ord-f580f5addbdb444abf447888ce2d05dc
Source dataset
uspto-grants-2016_02
Patent number
US09249084B2

Reaction notes

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