Toluene → Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate

HRID 1091762ノート

反応式

HRID 1091762 の反応式
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.Cl[CH2:19][C:20]([N:22]([CH3:24])[CH3:23])=[O:21].C1(C)C=CC=CC=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:23][N:22]([CH3:24])[C:20](=[O:21])[CH2:19][O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

参加物

7

反応物 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 758862-chloro-N,N-dimethylacetamideHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylate

生成物 1

HCID 57791803Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate収率 88.1%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

Benzyl 4-hydroxypiperidine-1-carboxylate (5 g, 21.25 mmol), tetrabutylammonium hydrogensulfate (0.361 g, 1.06 mmol) and 2-chloro-N,N-dimethylacetamide (4.13 g, 27.63 mmol) were added to toluene (50 mL) to this was added sodium hydroxide (21 g, 210.02 mmol) in water (30 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford the desired compound as an orange liquid (6.00 g, 88% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.65-1.55 (2H, m), 1.93-1.86 (2H, m), 2.95 (3H, s), 3.03 (3H, s), 3.25-3.18 (2H, m), 3.63-3.57 (1H, m), 3.85-3.79 (2H, m), 4.17 (2H, s), 5.12 (2H, s), 7.38-7.30 (5H, m).

後処理

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated

出典と根拠

ORDレコード
ord-e753dd91363d42ad809fdc46c4ef484c
出典データセット
uspto-grants-2012_03
特許番号
US08129380B2

反応ノート

読み込み中…