Hydrochloric Acid → HCID 70025612, compound

HRID 397590Notes

Reaction equation

HRID 397590 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.[Cl:34][CH2:35][CH2:36][N:37]1[CH2:41][CH2:40][CH2:39][CH2:38]1.Cl>CC(C)=O>[ClH:34].[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][CH2:35][CH2:36][N:37]3[CH2:41][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 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 12114663HCID 12114663, compound

Product 1

HCID 70025612HCID 70025612, 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, 0.001 mol), anhydrous K2CO3 (2.0 gm, 0.14 mol), 1-(2-chloroethyl)pyrrolidine 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 the 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 using benzene as the eluent, and concentrated to give an oil. The oil thus obtained was treated with ethanolic HCl. The solvent was evaporated and the compound was crystallized with absolute alcohol and dry ether, filtered under anhydrous conditions, and dried to give the title compound of formula I. Yield 350 mg. (68.35%).

Workup

  1. temperaturewas refluxed for 10 hrs
  2. filtrationK2CO3 was filtered off
  3. distillationacetone was distilled off
  4. additionthe residue 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. concentrationconcentrated
  12. customto give an oil
  13. customThe oil thus obtained
  14. customThe solvent was evaporated
  15. customthe compound was crystallized with absolute alcohol and dry ether
  16. filtrationfiltered under anhydrous conditions
  17. customdried

Sources & evidence

ORD record
ord-7d0f94d9d3e44f81a8ebbee67c562b3f
Source dataset
uspto-grants-2003_08
Patent number
US06610705B1

Reaction notes

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