1-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazine → HCID 20132434, compound

HRID 845221Notes

Reaction equation

HRID 845221 reaction equation
ClC1C=CC(C(C2C=C(C=CC=2)/C=C/[C:19]([OH:21])=[O:20])N2CCN(C)CC2)=CC=1.Br[C:28]1[CH:29]=[C:30]([CH:46]=[CH:47][CH:48]=1)[CH:31]([N:39]1[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]1)[C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1>O1CCCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH:31]([C:30]2[CH:29]=[C:28]([CH:48]=[CH:47][CH:46]=2)[C:19]([OH:21])=[O:20])[N:39]2[CH2:44][CH2:43][N:42]([CH3:45])[CH2:41][CH2:40]2)=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 189559271-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazineHCID 20132436HCID 20132436, compound

Product 1

HCID 20132434HCID 20132434, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The intermediate from Example 1, 1-(3-bromo-4'-chlorobenzhydryl)-4-methylpiperazine (1.10 g, 2.90 mmol), was dissolved in 10 mL of dry tetrahydrofuran and dried further over 4A molecular sieves for 24 hours. The solution was transferred to a dry flask under nitrogen and cooled to -78°. n-Butyllithium in hexane (1.1M, 2.6 ml) was added dropwise and the solution was stirred for 10 minutes at -78°. Carbon dioxide gas was bubbled into the reaction until the red solution turned yellow. The reaction was warmed to room temperature and the solvent was evaporated. The residue was dissolved in 20 mL of water and made basic with several drops of 1M sodium hydroxide. The aqueous solution was extracted with two 50 mL portion of ether and the pH was adjusted to 7-8 with 1M hydrochloric acid. After chilling in an ice bath, the precipitate was collected by filtration to give 341 mg (33%) of 3-(4-chloro-α-(4-methyl-1-piperazinyl)benzyl)benzoic acid as a white powder, m.p. 225°-230° (dec.). Calc. for C19H21ClN2O2. 0.75 H2O: C, 63.68; H, 6.33; N, 7.82; Cl, 9.89. Found: C, 63.68; H, 6.34; N, 7.82; Cl, 9.89.

Workup

  1. dry with materialdried further over 4A molecular sieves for 24 hours
  2. customThe solution was transferred to a dry flask under nitrogen
  3. temperaturecooled to -78°
  4. additionn-Butyllithium in hexane (1.1M, 2.6 ml) was added dropwise
  5. customCarbon dioxide gas was bubbled into the reaction until the red solution
  6. customthe solvent was evaporated
  7. dissolutionThe residue was dissolved in 20 mL of water
  8. extractionThe aqueous solution was extracted with two 50 mL portion of ether
  9. temperatureAfter chilling in an ice bath
  10. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-db8c316f15e24042b681189d8b8cc9ed
Source dataset
uspto-grants-1988_07
Patent number
US04757074

Reaction notes

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