Triethylamine → Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine

HRID 1190117ノート

反応式

HRID 1190117 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11](Cl)(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][C@H:16]1[CH2:21][NH:20][CH2:19][C@@H:18]([CH3:22])[NH:17]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:15][C@H:16]1[NH:17][C@@H:18]([CH3:22])[CH2:19][N:20]([S:11]([CH2:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)(=[O:13])=[O:12])[CH2:21]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2794642(4-Nitrophenyl)methanesulfonyl chlorideHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

生成物 1

HCID 58994592Cis-3,5-dimethyl-1-(4-nitro-phenylmethanesulfonyl)-piperazine収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 250 mg (1.06 mmol) of 4-nitrophenylmethanesulfonyl chloride and 133 mg (1.17 mmol) of cis-2,6-dimethylpiperazine in CH2Cl2 (10 mL) was treated with 325 μL (2.33 mmol) of triethylamine at RT for 20 min. The mixture was diluted with CH2Cl2 (15 mL) and washed with water (1×15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo to afford 298 mg (90%) of the title compound as an off-white solid: 1H-NMR (CDCl3; 400 MHz): δ 8.25 (d, 2H, J=8.8 Hz), 7.87 (d, 2H, J=8.8 Hz), 4.24 (s, 1H), 3.59-3.53 (m, 2H), 2.92-2.82 (m, 2H), 2.30-2.23 (m, 2H), 1.04 (d, 6H, J=6.0 Hz). Mass spectrum (ESI, m/z): Calcd. for C13H19N3O4S, 314.1 (M+H). found 314.1.

後処理

  1. washwashed with water (1×15 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-18752a97214e4716b5208ada6c60d1ac
出典データセット
uspto-grants-2014_03
特許番号
US08674100B2

反応ノート

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