1-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazine → HCID 20132434、化合物

HRID 845221ノート

反応式

HRID 845221 の反応式
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

参加物

4

反応物 2

HCID 189559271-[(3-Bromophenyl)(4-chlorophenyl)methyl]-4-methylpiperazineHCID 20132436HCID 20132436、化合物

生成物 1

HCID 20132434HCID 20132434、化合物収率 33%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db8c316f15e24042b681189d8b8cc9ed
出典データセット
uspto-grants-1988_07
特許番号
US04757074

反応ノート

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