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

HRID 1822983Notes

Reaction equation

HRID 1822983 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), 1.8–1.9 (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-b1b7573c4b634030afd6d8227b09c170
Source dataset
uspto-grants-2006_05
Patent number
US07037932B2

Reaction notes

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