1-Methylpiperazine → HCID 131728505, compound

HRID 1927525Notes

Reaction equation

HRID 1927525 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:35])[C:15]2[O:21][C:20]3[C:22]([Cl:31])=[CH:23][C:24]([NH:26][C:27](=[O:30])[CH2:28]Cl)=[CH:25][C:19]=3[CH2:18][S:17](=[O:33])(=[O:32])[C:16]=2[CH:34]=1)=[O:11]>CN(C=O)C>[CH3:8][O:9][C:10]([C:12]1[CH:13]=[C:14]([CH3:35])[C:15]2[O:21][C:20]3[C:22]([Cl:31])=[CH:23][C:24]([NH:26][C:27](=[O:30])[CH2:28][N:5]4[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]4)=[CH:25][C:19]=3[CH2:18][S:17](=[O:32])(=[O:33])[C:16]=2[CH:34]=1)=[O:11]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 116336414-Chloro-2-(2-chloro-acetylamino)-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Product 1

HCID 131728505HCID 131728505, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Methyl piperazine (0.140 g, 0.675 mmol) was added to a solution of Example 133 (0.3 g, 1 mmol) in DMF (1 mL) and refluxed for 1.5 h. The reaction mixture was concentrated, treated with water and filtered to obtain the crude title compound, which was purified using flash chromatography (silica gel). Yield: 0.237 g, (70%); 1H NMR (DMSO-d6): δ 2.2 (s, 3H, CH3), 2.4 (s, 4H, 2CH2), 2.8 (s, 4H, 2CH2), 3.2 (s, 2H, CH2), 3.9 (s, 3H, CH3), 5.2 (s, 2H, CH2). 7.8 (s 1H Ar), 7.9 (s, 1H, Ar), 8.2 (s, 1H, Ar); MS: m/e (ES+) 508 (M+1).

Workup

  1. temperaturerefluxed for 1.5 h
  2. concentrationThe reaction mixture was concentrated
  3. additiontreated with water
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ea44edd833c84abf990000352f360e87
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

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