Hydrochloric Acid → HCID 10127387, compound

HRID 397591Notes

Reaction equation

HRID 397591 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Cl.ClC[CH2:36][N:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]1.Cl>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:41][CH2:42][N:37]3[CH2:36][CH2:40][CH2:39][CH2:38]3)=[CH:24][CH:25]=2)[CH:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 12114663HCID 12114663, compound

Product 1

HCID 10127387HCID 10127387, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of (4-methoxyphenyl)-(4-hydroxyphenyl)-1,2,3,4-tetrahydronaphth-1-yl-methane (400 mg 0.0011 mol), anhydrous K2CO3 (2.0 gm, 0.014 mol), 1-(2-chloroethyl)piperidine hydrochloride (400 mg, 0.002) and dry acetone (25.0 ml) was refluxed for 10 hrs, K2CO3 was filtered off acetone was distilled off and residue was diluted with water. The reaction mixture was extracted with ethyl acetate, washed with water, dried over sodium sulphate and concentrated to give an oil which was filtered through basic alumina column by using benzene as eluent, and was concentrated. The oil thus obtained was treated with ethanolic HCl. The solvent was evaporated and compound was crystallized with absolute alcohol and anhydrous ether, and filtered under anhydrous conditions to give title compound of formula I. Yield 310 mg. (58.6%).

Workup

  1. temperaturewas refluxed for 10 hrs
  2. filtrationK2CO3 was filtered off acetone
  3. distillationwas distilled off
  4. additionresidue was diluted with water
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customto give an oil which
  10. filtrationwas filtered through basic alumina column
  11. concentrationwas concentrated
  12. customThe oil thus obtained
  13. customThe solvent was evaporated
  14. customcompound was crystallized with absolute alcohol and anhydrous ether
  15. filtrationfiltered under anhydrous conditions

Sources & evidence

ORD record
ord-09416c980e3941ba9f0ce52ae3e5d44d
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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