Potassium Carbonate → Toluene-4-thiosulfonic acid S-[3-(4-methyl-piperazin-1-yl)-propyl]ester

HRID 707677Notes

Reaction equation

HRID 707677 reaction equation
Cl[CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)(=[O:8])=[O:7].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:2][CH2:3][CH2:4][S:5][S:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)(=[O:8])=[O:7])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 67607671Toluene-4-thiosulfonic acid S-(3-chloropropyl)ester

Product 1

HCID 67608237Toluene-4-thiosulfonic acid S-[3-(4-methyl-piperazin-1-yl)-propyl]ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Toluene-4-thiosulfonic acid S-(3-chloro-propyl) ester (4.9 g, 18.4 mol, 1.00 eq.), N-methylpiperazine (1.9 g, 19.3 mmol) 1.05 eq.) and potassium carbonate (2.7 g, 19.4 mmol, 1.05 eq.) were stirred together in acetonitrile (100 mL) at room temperature for 64 hours. The mixture was concentrated and the residue was partitioned between ethyl acetate (500 ml) and water (250 ml). The organic solution was washed with water (2×200 mL), dried using MgSO4, concentrated and purified by MPLC to give a light yellow oil weighing 2.1 g (36%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between ethyl acetate (500 ml) and water (250 ml)
  3. washThe organic solution was washed with water (2×200 mL)
  4. customdried
  5. concentrationconcentrated
  6. custompurified by MPLC
  7. customto give a light yellow oil

Sources & evidence

ORD record
ord-5e979d64bdb04b50b254a4f59083e782
Source dataset
uspto-grants-2015_11
Patent number
US09175042B2

Reaction notes

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