2,3-Dichloropyridine → Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate

HRID 1868009ノート

反応式

HRID 1868009 の反応式
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][N:16]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:21][C:20]1[C:15]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[N:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 11630777Tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate収率 20%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

tert-butyl piperazine-1-carboxylate (1.0 g, 5.37 mmol) and 2,3-dichloropyridine (795 mg, 5.37 mmol) charged to a microwave vial was added with diisopropylethylamine (2.34 mL, 13.42 mmol) and DMF (1.0 mL). The reaction mixture was subject to microwave irradiation at 165° C. for 30 minutes. The reaction was repeated six times in order to scale up. Combined reaction mixture was partitioned between EtOAc and water, organic layer washed with brine and dried over MgSO4. The crude product obtained by solvent evaporation was purified via flash column chromatography. tert-butyl 4-(3-chloropyridin-2-yl)piperazine-1-carboxylate was obtained in 20% yield (1.9 g) as yellow oil.

後処理

  1. customirradiation at 165° C. for 30 minutes
  2. customreaction mixture
  3. customwas partitioned between EtOAc and water, organic layer
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe crude product obtained by solvent evaporation
  7. customwas purified via flash column chromatography

出典と根拠

ORDレコード
ord-8be30edf93144e5f8fedce5618504a51
出典データセット
uspto-grants-2009_12
特許番号
US07632838B2

反応ノート

読み込み中…