4-Toluenesulfonyl chloride → HCID 54022066, compound

HRID 235121Notes

Reaction equation

HRID 235121 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1.CO.C(OCC)(=O)C>C1COCC1>[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[C:9]3[N:12]3[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]3)=[CH:4][CH:3]=2)(=[O:34])=[O:33])=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21584119Ethylacetate methanolHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 54022066HCID 54022066, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.205 g, 0.85 mmol) and triethylamine (0.124 mL, 0.935 mmol) in dry THF (3 mL) was chilled to 0° C and para toluenesulfonyl chloride (0.178 g, 0.935 mmol) was added all at once. The mixture was allowed to warm to room temperature and stirred overnight (TLC with 40% methanol/ethyl acetate indicated that the reaction was complete.) The solvent was removed at reduced pressure and the residue was taken up in methylene chloride. The organic solution was extracted with saturated sodium bicarbonate and brine, then it was dried over calcium sulfate and concentrated. Flash chromatography on silica gel (1×3 inches) with ethyl acetate/hexane gradient elution of from 50% to 100% gave 0.21 g of a light tan solid. The solid was further purified by two recrystallizations from ethyl acetate to yield 0.07 g (20%) of the title product: mp 180°-1 81.5° C. Analysis calculated for C22H25N3O2S: C, 66.81; H, 6.37; N, 10.62. Found: C, 66.55; H, 6.31; N, 10.20.

Workup

  1. custom) The solvent was removed at reduced pressure
  2. extractionThe organic solution was extracted with saturated sodium bicarbonate and brine
  3. dry with materialit was dried over calcium sulfate
  4. concentrationconcentrated
  5. washFlash chromatography on silica gel (1×3 inches) with ethyl acetate/hexane gradient elution of from 50% to 100%

Sources & evidence

ORD record
ord-d32e445c43a748a0bfe47aeb55efb38f
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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