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

HRID 1868009

반응식

HRID 1868009 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8be30edf93144e5f8fedce5618504a51
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632838B2

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