Potassium Iodide → HCID 22998314, compound

HRID 1276401Notes

Reaction equation

HRID 1276401 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.C(#N)C.[Cl:12][CH2:13][CH2:14][CH2:15][N:16]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH2:20][CH2:19][C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]1=2.[I-].[K+]>O>[ClH:12].[CH:27]1[C:18]2[CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[N:16]([CH2:15][CH2:14][CH2:13][N:5]3[CH2:6][CH2:7][CH2:8][CH:3]([CH2:2][OH:1])[CH2:4]3)[C:17]=2[CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 107308Piperidin-3-ylmethanolHCID 2867795-(3-Chloropropyl)-10,11-dihydro-5H-dibenz[b,f]azepine

Product 1

HCID 22998314HCID 22998314, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(hydroxymethyl)piperidine (1.01 g, 0.0088 mol), acetonitrile (9 ml), 5-(3-chloropropyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (0.86 g, 0.003 mol, pre-pared similarly as described in example 1) and potassium iodide (0.56 g, 0.003 mol) was heated at reflux temperature for 18 h. Water (20 ml) was added, and the mixture was extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with brine (2×20 ml), dried (MgSO4) and concentrated in vacuo. The residue was redissolved in a mixture of water (20 ml) and concentrated hydrochloric acid (3 ml), and extracted with dichloromethane (3×10 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4) and concentrated in vacuo. The residue was crystallised from a mixture of methanol (0.5 ml) and ethyl acetate (5 ml), affording 0.8 g (61%) of the title compound as needles.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 18 h
  3. extractionthe mixture was extracted with ethyl acetate (3×15 ml)
  4. washThe combined organic extracts were washed with brine (2×20 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was redissolved in a mixture of water (20 ml) and concentrated hydrochloric acid (3 ml)
  8. extractionextracted with dichloromethane (3×10 ml)
  9. washThe combined organic extracts were washed with brine (20 ml)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was crystallised from a mixture of methanol (0.5 ml) and ethyl acetate (5 ml)

Sources & evidence

ORD record
ord-d029c20c2c404087a84e1016a31b5de8
Source dataset
uspto-grants-2000_12
Patent number
US06166009

Reaction notes

Loading…