Benzoyl chloride → 1-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl ester

HRID 1013065ノート

反応式

HRID 1013065 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCOCC1.O.[Cl-].[Na+].O>[C:16]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 185197561-Piperazinecarboxylic acid, 4-benzoyl-, 1,1-diMethylethyl ester収率 90%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of N-Boc-piperazine (14) (1.00 g, 5.37 mmol) in dioxane (5 mL), a solution of NaOH (0.50 g, 12.9 mmol) in water (5 mL) followed by a solution of benzoyl chloride (0.75 mL, 6.44 mmol) in dioxane (2 mL) under vigorous stirring were added. The reaction mixture was stirred at ambient temperature for 4 hours, diluted with brine (20 mL), and extracted with ethyl acetate (2×25 mL). The organic extract was washed successively with brine (20 mL), saturated NaHCO3 (20 mL), saturated KH2PO4 (20 mL), and dried (Na2SO4). The solvents were evaporated to give the title compound (1.400 g, 90%) which was used in the next step of the synthesis without further purification. 1H NMR (CDCl3, HMDS), δ: 1.41 (s, 9H), 2.86 (t, J=5.0 Hz, 4H); 3.62 (t, J=5.0 Hz, 4H); 7.34 (s, 5H).

後処理

  1. additionwere added
  2. stirringThe reaction mixture was stirred at ambient temperature for 4 hours
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. extractionThe organic extract
  5. washwas washed successively with brine (20 mL), saturated NaHCO3 (20 mL), saturated KH2PO4 (20 mL)
  6. dry with materialdried (Na2SO4)
  7. customThe solvents were evaporated

出典と根拠

ORDレコード
ord-ed065e2b6a1b4a89a6369d2f5c1fbfd3
出典データセット
uspto-grants-2011_07
特許番号
US07981895B2

反応ノート

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