Potassium Carbonate → (S)-N-benzylidene-1-[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methylamine

HRID 369074Notes

Reaction equation

HRID 369074 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:17][C:16]3[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)(=O)=O)=CC=1.[CH:24](=[N:31][CH2:32][CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.[I-].[K+]>[CH:24](=[N:31][CH2:32][CH:33]1[CH2:34][CH2:35][N:36]([CH2:11][C@@H:12]2[O:17][C:16]3[CH:18]=[C:19]([Br:22])[CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)[CH2:37][CH2:38]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11820173N-Benzylidene(piperidin-4-yl)methanamineHCID 54071671(R)-7-bromo-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate

Product 1

HCID 54401525(S)-N-benzylidene-1-[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methylamine

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-7-bromo-1,4-benzodioxan-2-ylmethyl 4-toluenesulphonate (6.5 g, prepared as described in WO97/03071), N-benzylidene-4-piperidylmethylamine (3.0 g), potassium carbonate (4.1 g), and potassium iodide (10 mg) in acetonitrile (200 ml) was heated at reflux, with stirring, under nitrogen for 24 hours. The reaction was cooled, filtered and concentrated under reduced pressure to afford (S)-N-benzylidene-1-[1-(7-bromo-1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methylamine (6.3 g) as an orange-brown viscous oil.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux
  4. temperatureThe reaction was cooled
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92f1ff4b8956456084127daf68f79825
Source dataset
uspto-grants-2000_10
Patent number
US06136825

Reaction notes

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