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

HRID 1190117Notes

Reaction equation

HRID 1190117 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-18752a97214e4716b5208ada6c60d1ac
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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