Anisole → HCID 10340129, compound

HRID 370658

Reaction equation

HRID 370658 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:36])[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1(OC)C=CC=CC=1>C(O)(=O)C.Br>[C:30]1([CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:20]2[CH2:19][CH2:18][N:17]([CH2:16][C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)=[O:36])[CH2:22][CH2:21]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 7519AnisoleHCID 103227601-(4-Benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanone

Product 1

HCID 10340129HCID 10340129, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

12.5 g (26 mmol) of 1-(4-benzyloxyphenyl)-2-(4-diphenylmethyl-piperazinyl)ethanone and 2.8 g (26 mmol) of anisole were dissolved in a mixture of 37.5 ml of acetic acid and 12.5 ml of 47% hydrobromic acid. The resultant mixture was heated to reflux for 1 hour. After being cooled to room temperautre, the reaction mixture was washed with 200 ml of ether and then with 50 ml of ether to remove acetic acid. The resultant solution was neutralized with an aqueous 2N solution of sodium hydroxide. Separated organic substances were extracted with 120 ml of ethyl acetate and then washed with saturated saline. The ethyl acetate solution was dried over anhydrous sodium sulfate and then concentrated. The residue was taken up in 60 ml of isopropanol and allowed to stand at room temperature to give 6.28 g of crude crystals of 2-(4-diphenylmethylpiperazinyl)-1-(4-hydroxyphenyl)ethanone (yield: 62%).

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureAfter being cooled to room temperautre
  3. washthe reaction mixture was washed with 200 ml of ether
  4. customwith 50 ml of ether to remove acetic acid
  5. extractionSeparated organic substances were extracted with 120 ml of ethyl acetate
  6. washwashed with saturated saline
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto stand at room temperature

Sources & evidence

ORD record
ord-ff844af5aea943b1b43f1a93ac133f60
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Linked notes

Loading…