Hydrochloric Acid → HCID 22273770, compound

HRID 1064383Notes

Reaction equation

HRID 1064383 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[CH:16](O)[CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:26].[OH-].[Na+]>O1CCOCC1>[ClH:26].[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:14]3[CH:15]=[CH:16][C:17]4[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=4[CH2:19][CH2:20]3)[CH2:11][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22273755HCID 22273755, compound

Product 1

HCID 22273770HCID 22273770, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.2 g (0.6 mmol) of (±)-7-[(4-phenylpiperidin-1-yl)methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol were dissolved in 5 mL of 1,4-dioxane and 16 mL of 37% HCl and heated to reflux for 2 h. The reaction mixture was then basified with NaOH and extracted with CH2Cl2. The organic phase was dried and the solvent was removed in vacuo. The resulting crude product was purified by chromatography, eluting with a mixture CH2Cl2/MeOH 100:2 respectively; The compound was dissolved in Et2O and brought to acidic pH with Et2O/HCl. The resulting white solid was triturated with Et2O, filtered and dried, yielding 0.02 g of the title compound. m.p.=268-270° C.

Workup

  1. temperatureto reflux for 2 h
  2. extractionextracted with CH2Cl2
  3. customThe organic phase was dried
  4. customthe solvent was removed in vacuo
  5. customThe resulting crude product was purified by chromatography
  6. washeluting with a mixture CH2Cl2/MeOH 100:2 respectively
  7. dissolutionThe compound was dissolved in Et2O
  8. customThe resulting white solid was triturated with Et2O
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-5650a1e0bc674e3798dd9868e9ac12f6
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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