p-Toluenesulfonic acid monohydrate → 4-[2-(Dimethylamino)thiazol-4-yl]-4-phenylpiperidine p-toluenesulfonate

HRID 1066647ノート

反応式

HRID 1066647 の反応式
Br.Br[CH2:3][C:4]([C:6]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=O.[CH3:18][N:19]([CH3:23])[C:20]([NH2:22])=[S:21].O.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1>CCO.CC(C)=O>[C:25]1([CH3:35])[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:32])=[O:33])=[CH:29][CH:30]=1.[CH3:18][N:19]([CH3:23])[C:20]1[S:21][CH:3]=[C:4]([C:6]2([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:22]=1

参加物

6

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 30341921,1-Dimethyl-2-thioureaHCID 227417564-(2-Bromoacetyl)-4-phenylpiperidine hydrobromide

生成物 1

HCID 212005544-[2-(Dimethylamino)thiazol-4-yl]-4-phenylpiperidine p-toluenesulfonate収率 76.3%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒2 回HCID 702Ethanol溶媒

実験手順

A mixture of 7.26 g of the compound obtained in step B) and 2.08 g of the compound obtained in step A) in 150 ml of EtOH is refluxed for 1 hour 30 minutes. After cooling to RT, the mixture is concentrated under vacuum, the residue is taken up with water, rendered alkaline to pH 10 by the addition of 10% NaOH solution and extracted with DCM, the organic phase is washed with 10% NaOH solution and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The product obtained is dissolved in acetone, a solution of 3.31 g of p-toluenesulfonic acid monohydrate in 10 ml of acetone is added dropwise and the crystalline product formed is wrung to give 6.1 g of the expected product. M.p.=164° C.

後処理

  1. temperatureis refluxed for 1 hour 30 minutes
  2. concentrationthe mixture is concentrated under vacuum
  3. additionby the addition of 10% NaOH solution
  4. extractionextracted with DCM
  5. washthe organic phase is washed with 10% NaOH solution and with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated off under vacuum
  8. customThe product obtained
  9. customthe crystalline product formed

出典と根拠

ORDレコード
ord-fe0976a179a34e3ca3d86cdcb9a8e85d
出典データセット
uspto-grants-2001_06
特許番号
US06242637B1

反応ノート

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