2-Bromobenzoic acid → Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate

HRID 1665584ノート

反応式

HRID 1665584 の反応式
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.CCN=C=NCCCN(C)C.Cl.[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:44])[CH3:43]>CN(C=O)C.O>[C:42]([O:46][C:47]([N:49]1[CH2:54][CH2:53][N:52]([C:23](=[O:25])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[Br:20])[CH2:51][CH2:50]1)=[O:48])([CH3:45])([CH3:43])[CH3:44]

参加物

8

反応物 5

HCID 69402-Bromobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

生成物 1

HCID 17952334Tert-butyl 4-(2-bromobenzoyl)piperazine-1-carboxylate収率 90.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

HOBt (4 g, 29.6 mmol) and DIEA (8.7 g, 67.7 mmol) were added to a stirred solution of 2-bromo benzoic acid (5.6 g, 28.3 mmol) in DMF (50 mL). The reaction mixture was cooled to 10° C. and EDCI.HCl (7.76 g, 40.48 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (5 g, 26.9 mmol) were added. Then reaction mixture was stirred at the room temperature overnight. Water was added and the product was extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over Na2SO4, and removed under reduced pressure to afford 9 g (90%) of 4-(2-bromo-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. 1H NMR: (DMSO-d6): δ 7.58 (d, 1H), 7.38 (t, 1H), 7.29 (d, 1H), 7.24 (d, 1H), 3.85 (m, 1H), 3.7 (m, 1H), 3.55 (t, 2H), 3.5 (m, 1H), 3.3 (m, 3H), 3.15 (m, 1H), 1.45 (s, 9H).

後処理

  1. additionwere added
  2. customThen reaction mixture
  3. extractionthe product was extracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. customremoved under reduced pressure

出典と根拠

ORDレコード
ord-334e494e16b343ddb98163ad28039856
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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