1-Methylpiperazine → HCID 70161439, compound

HRID 1251074Notes

Reaction equation

HRID 1251074 reaction equation
[F:1][C:2]1([F:27])[CH2:3][CH2:4][N:5]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2/[C:8]/1=[CH:9]/[C:10]([OH:12])=O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[CH3:50][N:51]1[CH2:56][CH2:55][NH:54][CH2:53][CH2:52]1>O1CCCC1>[F:1][C:2]1([F:27])[CH2:3][CH2:4][N:5]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:18])=[O:19])[C:6]2[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=2/[C:8]/1=[CH:9]/[C:10]([N:54]1[CH2:55][CH2:56][N:51]([CH3:50])[CH2:52][CH2:53]1)=[O:12]

Participants

6

Reactant 4

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11463508HCID 11463508, compound

Product 1

HCID 70161439HCID 70161439, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10 g of (Z)-(4,4-difluoro-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene)acetic acid in 100 ml of tetrahydrofuran were added 4.12 g of 1-hydroxybenzotriazole, 5.85 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 3.36 ml of 1-methylpiperazine, followed by stirring for two hours at room temperature. After evaporation of the solvent, ethyl acetate was added to the residue, and the mixture was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of NaCl. After drying over magnesium sulfate, the solvent was evaporated off. The resulting residue was collected by filtration to give 11.76 g of (Z)-4,4-difluoro-5-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]-1-tosyl-2,3,4,5-tetrahydro-1H-1-benzoazepine as a colorless amorphous solid.

Workup

  1. customAfter evaporation of the solvent, ethyl acetate
  2. additionwas added to the residue
  3. washthe mixture was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialAfter drying over magnesium sulfate
  5. customthe solvent was evaporated off
  6. filtrationThe resulting residue was collected by filtration

Sources & evidence

ORD record
ord-f5153c8f6e744001a3e861ff45359b82
Source dataset
uspto-grants-2002_01
Patent number
US06340678B1

Reaction notes

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