Potassium Carbonate → HCID 54531367、化合物

HRID 582551ノート

反応式

HRID 582551 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH:15]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:16][CH2:17][C:18]#[N:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:17][C:18]#[N:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 54247840HCID 54247840、化合物

生成物 1

HCID 54531367HCID 54531367、化合物収率 88%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 1-(tert-butyloxycarbonyl)piperazine (1.73 g, 9.3 mmol), 4-bromo-4-phenylbutyronitrile (2.5 g, 11 mmol) and K2CO3 (1.4 g, 10.2 mmol) in DMF (40 mL) was heated at 60° C. for 4 h. After this time the mixture was cooled to room temperature, filtered and the filtrate evaporated. The residue was partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with petrol:EtOAc (2:1). The piperazine (2.69 g, 88%) was isolated as a pale yellow oil, which solidified on standing in the fridge. 1H NMR (250 MHz, CDCl3) δ1.41 (9H, s), 1.94-2.46 (8H, m), 3.32-3.60 (5H, m), 7.15-7.42 (5H, m). MS (ES+) (330, M+1).

後処理

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between EtOAc (100 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with petrol:EtOAc (2:1)

出典と根拠

ORDレコード
ord-df2973ac3e554307beb29dee16328407
出典データセット
uspto-grants-1999_07
特許番号
US05925638

反応ノート

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