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

HRID 1190117노트

반응식

HRID 1190117 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-18752a97214e4716b5208ada6c60d1ac
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674100B2

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