Bromomethyl 4-methoxyphenyl ketone → 1-[2-(4-Methoxyphenyl)-2-oxoethyl]-4-(4-naphthalen-1-yl-butyl)piperazine

HRID 497318Notes

Reaction equation

HRID 497318 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.Cl.Cl.[C:24]1([CH2:34][CH2:35][CH2:36][CH2:37][N:38]2[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]2)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][N:41]2[CH2:40][CH2:39][N:38]([CH2:37][CH2:36][CH2:35][CH2:34][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=[CH:26][CH:25]=3)[CH2:43][CH2:42]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 81531DiisopropylethylamineHCID 223186681-(4-Naphthalen-1-yl-butyl)piperazine dihydrochloride

Product 1

HCID 223186411-[2-(4-Methoxyphenyl)-2-oxoethyl]-4-(4-naphthalen-1-yl-butyl)piperazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 6.0 ml of chloroform was dissolved 0.69 g of 4-methoxyphenacyl bromide, and 3.0 ml of N-ethyldiisopropylamine and 1.20 g of 1-(4-naphthalen-1-yl-butyl)piperazine dihydrochloride were added, followed by reflux with heating for an hour. The reaction solution was cooled to room temperature, and concentrated under reduced pressure. To the residue was added a saturated aqueous sodium bicarbonate solution and, after extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure to give a crude 1-[2-(4-methoxyphenyl)-2-oxoethyl]-4-(4-naphthalen-1-yl-butyl)piperazine.

Workup

  1. additionwere added
  2. temperatureby reflux
  3. temperaturewith heating for an hour
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added a saturated aqueous sodium bicarbonate solution
  6. extractionafter extraction with ethyl acetate
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c20a66ae5584af3b12c9de088dc9b57
Source dataset
uspto-grants-2005_09
Patent number
US06949552B2

Reaction notes

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