3-Methylbenzylpiperazine → HCID 18955924、化合物

HRID 893287ノート

反応式

HRID 893287 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:35]=[CH:36][CH:37]=1)[CH:26](Cl)[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.C(OCC)C>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:35]=[CH:36][CH:37]=1)[CH:26]([N:9]1[CH2:8][CH2:7][N:6]([CH2:5][C:4]2[CH:12]=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=2)[CH2:11][CH2:10]1)[C:27]1[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

5

反応物 2

HCID 792133-MethylbenzylpiperazineHCID 18955928HCID 18955928、化合物

生成物 1

HCID 18955924HCID 18955924、化合物収率 53%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 3283Diethyl Ether溶媒

実験手順

The crude piperazine derivative from above (11.0 g, 56 mmole) was dissolved in 150 ml of toluene and added to 19.2 g (56 mmole) of 3-benzyloxy-4'-chlorobenzhydryl chloride (see U.S. Pat. No. 4,757,074) and heated to reflux for 40 hours. The reaction was cooled to room temperature, diluted to 600 ml with diethyl ether, and washed with 100 ml of 1.0 M sodium hydroxide followed by three 200 ml portions of water and 100 ml of saturated sodium chloride. The product was dried over sodium sulfate and the solvent removed to give 27.0 g of crude product as a dark oil. The material was purified by chromatography on silica gel (Waters Prep 500) with 0.1% triethylamine in dichloromethane to give 14.7 g (53%) of 1-(3-benzyloxy-4'-chlorobenzhydryl)-4-(3-methylbenzyl) piperazine as a dark oil. A 5.0 g portion of the oil was dissolved in 00 ml of 2:1 ethanol:methanol and treated with an excess of ethanolic hydrochloric acid to produce the dihydrochloride salt of the product. Addition of 150 ml diethyl ether and cooling provided 1.74 g of the salt as white crystals, mp. 204°-208° C. Calc. for C32H33ClN2O 2HCl: C, 67.43; H, 6.19; N, 4.91; Cl, 18.66. Found: C, 67.15; H, 6.14; N, 4.87; Cl, 18.58.

後処理

  1. temperature4,757,074) and heated
  2. temperatureto reflux for 40 hours
  3. washwashed with 100 ml of 1.0 M sodium hydroxide
  4. dry with materialThe product was dried over sodium sulfate
  5. customthe solvent removed
  6. customto give 27.0 g of crude product as a dark oil
  7. customThe material was purified by chromatography on silica gel (Waters Prep 500) with 0.1% triethylamine in dichloromethane

出典と根拠

ORDレコード
ord-e44f66abc49341ccbf4fad32b0c9018b
出典データセット
uspto-grants-1992_06
特許番号
US05124330

反応ノート

読み込み中…