Pyridinium chloride → HCID 11638405, compound

HRID 624511Notes

Reaction equation

HRID 624511 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[C:11]1[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=3[S:8][CH2:7][C:6]2=1.Cl.N1C=CC=CC=1>>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][N:12]1[C:11]2[C:10]3[CH:21]=[CH:22][CH:23]=[CH:24][C:9]=3[S:8][CH2:7][C:6]=2[C:5]2[C:13]1=[CH:14][CH:15]=[C:3]([OH:2])[CH:4]=2

Participants

3

Reactant 2

HCID 10176127Pyridinium chlorideHCID 11681613HCID 11681613, compound

Product 1

HCID 11638405HCID 11638405, compound

Conditions

Temperature
210 °C

Procedure

A mixture of [2-(8-methoxy-6H-5-thia-11-aza-benzo[a]fluoren-11-yl)-ethyl]-dimethyl-amine (800 mg, 2.39 mmol) and Pyridine HCl (3.01 g, 23.7 mmol, 10 eq.) was heated to 210° C. for 30 minutes. The reaction mixture was then partitioned between EtOAc and saturated NaHCO3 aqueous solution. The aqueous layer was extracted three times with EtOAc. The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a crude material. The crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1) to yield the title compound as a brown solid.

Workup

  1. customThe reaction mixture was then partitioned between EtOAc and saturated NaHCO3 aqueous solution
  2. extractionThe aqueous layer was extracted three times with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude material
  8. customThe crude material was purified by silica gel (EtOAc to CH2Cl2: MeOH 5:1)

Sources & evidence

ORD record
ord-38a89a185e4e460881a292cb136ce798
Source dataset
uspto-grants-2016_04
Patent number
US09303037B2

Reaction notes

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