Diisopropylamine → N-(4-n-butoxyphenyl)-N-methyl-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide

HRID 49960ノート

反応式

HRID 49960 の反応式
[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([N:10]([CH3:14])[C:11](=[O:13])[CH3:12])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:37]([N:44]1[CH2:49][CH2:48][C:47](=[O:50])[CH2:46][CH2:45]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>O1CCCC1.O>[CH2:1]([O:5][C:6]1[CH:16]=[CH:15][C:9]([N:10]([CH3:14])[C:11](=[O:13])[CH2:12][C:47]2([OH:50])[CH2:48][CH2:49][N:44]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:45][CH2:46]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

参加物

8

反応物 5

HCID 7912DiisopropylamineHCID 192201-Benzyl-4-piperidoneHCID 2724682Lithium diisopropylamideHCID 17823826HCID 17823826、化合物HCID 178418339Butyllithium

生成物 1

HCID 9931398N-(4-n-butoxyphenyl)-N-methyl-2-(1-benzyl-4-hydroxypiperidin-4-yl)acetamide収率 52.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 4′-n-butoxy-N-methylacetanilide (0.34 g) in anhydrous tetrahydrofuran (1.5 mL) was added to a solution of lithium diisopropylamide prepared from diisopropylamine (0.22 mL) and n-butyl lithium (1.58M hexane solution; 1.07 mL) in an anhydrous tetrahydrofuran (1.6 mL) under cooling with ice-water, and the mixture was stirred for 30 minutes. A solution of 1-benzylpiperidin-4-one (0.32 g) in anhydrous tetrahydrofuran solution (1.5 mL) was added to thereto under cooling with ice-water, followed by additional stirring for 30 minutes. After increasing the temperature to room temperature, water was added to the mixture and extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was distilled off. The titled compound (0.33 g) was obtained by recrystallization of the residue from hexane.

後処理

  1. stirringby additional stirring for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off

出典と根拠

ORDレコード
ord-756478f821114d2aab54a92d47d79ef3
出典データセット
uspto-grants-2004_03
特許番号
US06710060B2

反応ノート

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