Hydrochloric Acid → HCID 9889539, compound

HRID 413285Notes

Reaction equation

HRID 413285 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([CH2:12]O)[N:9]=[CH:8]2)=[CH:4][CH:3]=1.C([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])C.S(Cl)(Cl)=O.Cl.[C:28]1([CH3:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([CH2:12][N:18]3[CH2:19][CH2:20][C:34]([C:2]4[CH:15]=[CH:14][CH:5]=[CH:4][CH:3]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:22][CH2:21]3)[N:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 18523584HCID 18523584, compound

Product 1

HCID 9889539HCID 9889539, compound

Procedure

The product of step (a) (0.39 g) was dissolved in toluene (10 ml), triethylamine (0.26 ml) and thionyl chloride (0.13 ml) were added and the mixture stirred at room temperature for 20 hours. The solvent was removed by evaporation, a solution of 4,4-diphenylpiperidine hydrochloride (0.478 g) in dimethylsulphoxide (10 ml) and triethylamine (0.65 ml) added. After 2 hours water and ethyl acetate were added, the organic phase was separated, washed with brine, dried and the solvent removed to leave a gum. Purification by supercritical fluid chromatography gave a solid which was treated with 1.0M ethereal hydrogen chloride solution to give the product as a solid (0.02 g), m.p. 254-255° C.

Workup

  1. customThe solvent was removed by evaporation
  2. additiona solution of 4,4-diphenylpiperidine hydrochloride (0.478 g) in dimethylsulphoxide (10 ml) and triethylamine (0.65 ml) added
  3. additionAfter 2 hours water and ethyl acetate were added
  4. customthe organic phase was separated
  5. washwashed with brine
  6. customdried
  7. customthe solvent removed
  8. customto leave a gum
  9. customPurification by supercritical fluid chromatography
  10. customgave a solid which

Sources & evidence

ORD record
ord-3fc6aa18e66c44d380ef3eb0703677ae
Source dataset
uspto-grants-2003_05
Patent number
US06566376B1

Reaction notes

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