Triethylamine → N-[2-(Phenylsulfonyl)ethyl]-1-piperidineethanamine maleate

HRID 330393

反応式

HRID 330393 の反応式
Cl[CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:6])=[O:5].[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>C(#N)C.CO>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[C:7]1([S:4]([CH2:3][CH2:2][NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:6])=[O:5])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 13646((2-Chloroethyl)sulphonyl)benzeneHCID 33944N-(2-Aminoethyl)piperidineHCID 444266Maleic Acid

生成物 1

HCID 70360543N-[2-(Phenylsulfonyl)ethyl]-1-piperidineethanamine maleate収率 60.78%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

A mixture of 40.94 g (0.20 mole) of [(2-chloroethyl)sulfonyl]benzene, 27.85 g (0.217 mole) of N-(2-aminoethyl)piperidine and 28.0 g (0.277 mole) of triethylamine in 800 ml of acetonitrile was stirred at room temperature overnight. The solvent was removed in vacuo, and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in methanol, a solution of 2 equivalents of maleic acid in methanol was added, and the product crystallized from the solution at room temperatue to give 64.35 g (60.78%) of title compound as a white crystalline solid, mp 154°-155.5° C.

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methanol
  6. customthe product crystallized from the solution at room temperatue

出典と根拠

ORDレコード
ord-02a04086823f4a4e8450854c0a958793
出典データセット
uspto-grants-1990_01
特許番号
US04895840

関連ノート

読み込み中…