Hydrochloric Acid → HCID 131728578, compound

HRID 1260270Notes

Reaction equation

HRID 1260270 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:5]1)[CH2:2][CH3:3].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([Cl:29])(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18].C(N(CC)CC)C.Cl>O1CCCC1.C(OCC)C>[ClH:29].[CH:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:16][C:13]2[CH:12]=[CH:11][C:10]([CH:6]3[CH2:7][CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5]3)=[CH:15][CH:14]=2)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 57494450HCID 57494450, compound

Product 1

HCID 131728578HCID 131728578, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Propyl-piperidin-3-yl)-phenylamine (600 mg, 1.65 mmol) and 4-isopropyl-phenylsulfonyl chloride (397 mg, 1.81 mmol) were dissolved in tetrahydrofuran (25 ml). Triethylamine (760 μl, 5.44 mmol) was added and the reaction mixture stirred for 72 hours at room temperature. The solvent was evaporated under reduced pressure, the residue treated with diethyl ether (50 ml) and three times extracted with water (3×30 ml). The organic phase was treated with 1 molar HCl solution. The acidic aqueous solution was made alkaline with NaOH solution to pH 9-10 and then extracted with ethyl acetate (25 ml). The organic phase was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to give the crude product (580 mg). The crude product was purified via silica gel chromatography with ethyl acetate. Fractions containing the product were combined, the solvent evaporated to yield the pure product which was then converted into the hydrochloride salt via adding a solution of 1 N HCl in diethyl ether. The precipitate was filtered off and dried in vacuo to give the pure product (283 mg, 39%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue treated with diethyl ether (50 ml) and three times
  3. extractionextracted with water (3×30 ml)
  4. additionThe organic phase was treated with 1 molar HCl solution
  5. extractionextracted with ethyl acetate (25 ml)
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure
  9. customto give the crude product (580 mg)
  10. customThe crude product was purified via silica gel chromatography with ethyl acetate
  11. additionFractions containing the product
  12. customthe solvent evaporated
  13. customto yield the pure product which
  14. filtrationThe precipitate was filtered off
  15. customdried in vacuo

Sources & evidence

ORD record
ord-d08c493e994d4d5698c977490a6e65ae
Source dataset
uspto-grants-2013_06
Patent number
US08470810B2

Reaction notes

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