Potassium Iodide → (R,S)-N-Methyl 3-benzylamino-1-phenyl-1-propanol

HRID 2218080Notes

Reaction equation

HRID 2218080 reaction equation
Cl[CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[CH3:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:14]([N:13]([CH3:12])[CH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 5720643-Chloro-1-phenylpropanol

Product 1

HCID 15678556(R,S)-N-Methyl 3-benzylamino-1-phenyl-1-propanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-chloro-1-phenylpropan-1-ol (2 g, 11.7 mmol), N-methylbenzylamine (2.12 g, 17.5 mmol), potassium iodide (2.6 g, 22 mmol), and potassium carbonate (3.2 g, 23.4 mmol) in dimethylformamide (120 mL) was stirred at 90° C. in a reacti-vial for 16 h. After this time the reaction was allowed to cool to room temperature. The reaction mixture was purified by an SCX-2 column eluting with Methanol followed by ammonia:methanol solution (7 N). The organics were then evaporated and the compound taken directly onto the next step without any further purification. (M+H+1 [256]); δH (300 MHz, CDCl3) 7.2-7.4 (10H, m, Ar), 4.9 (1H, t, CH—OH), 3.55 (1H, d, CH2-Ph), 3.45 (1H, d, CH2—PH), 2.8-3 (1H, m, CH2), 2.55-2.65 (1H, m, CH2), 2.25 (3H, s, CH3), 1.89-1.9 (2H, m, CH2), 1.6 (1H, brs, OH).

Workup

  1. customThe reaction mixture was purified by an SCX-2 column
  2. washeluting with Methanol
  3. customThe organics were then evaporated
  4. customthe compound taken directly onto the next step without any further purification

Sources & evidence

ORD record
ord-1221cb40e051429b8ce8f73802e92aca
Source dataset
uspto-grants-2008_08
Patent number
US07410982B2

Reaction notes

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