Pyridinium chloride → HCID 118006345, compound

HRID 929282Notes

Reaction equation

HRID 929282 reaction equation
[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([C:27]1[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=1)[C:8]1[C:13]2[O:14][C:15]3[C:20]([CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1.Cl.N1C=CC=CC=1>>[C:1]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([C:8]1[C:13]2[O:14][C:15]3[C:20]([CH:21]4[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]4)=[CH:19][CH:18]=[CH:17][C:16]=3[C:12]=2[CH:11]=[CH:10][CH:9]=1)[C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 118006062HCID 118006062, compound

Product 1

HCID 118006345HCID 118006345, compoundYield 75%

Procedure

A mixture of N-([1,1′-biphenyl]-2-yl)-6-cyclohexyl-N-(4-methoxyphenyl)dibenzo[b,d]furan-4-amine (8.9 g, 17.0 mmol) and pyridine hydrochloride (19.6 g, 170.0 mmol) was purged with nitrogen overnight. The mixture was then refluxed for 2 h. After cooling, the precipitate was filtered and washed by excess water. The residue was purified by flash chromatography using 90% DCM/hexane (containing 1% triethylamine) to yield 4-([1,1′-biphenyl]-2-yl(6-cyclohexyldibenzo[b,d]furan-4-yl)amino)phenol (6.5 g, 75% yield) as a white solid.

Workup

  1. customwas purged with nitrogen overnight
  2. temperatureThe mixture was then refluxed for 2 h
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtered
  5. washwashed by excess water
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-9a5c386945304f54831c47a4e2728912
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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