4-Phenylbenzylamine → HCID 66717805, compound

HRID 241286Notes

Reaction equation

HRID 241286 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7](Cl)(=[O:9])=[O:8])[CH:2]=1.[C:11]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[CH:15][C:14]([CH2:17][NH2:18])=[CH:13][CH:12]=1>O>[C:11]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:12]=[CH:13][C:14]([CH2:17][NH:18][S:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)(=[O:9])=[O:8])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 3449894-PhenylbenzylamineHCID 3164136Pyridine-3-sulfonyl chloride

Product 1

HCID 66717805HCID 66717805, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reaction was carried out in the same manner as in Reference Example 2-(d) except for using 3-pyridylsulfonyl chloride (890 mg, 5.01 mmol), and using (biphenyl-4-ylmethyl)amine (1.01 g, 5.51 mmol) in place of (6-phenylpyridazin-3-ylmethyl)amine hydrochloride. After completion of the reaction, water was added to the reaction solution, followed by extraction with ethyl acetate. The separated organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:1 (V/V)→chloroform:ethyl acetate=1:1 (V/V)→ethyl acetate), and fractions containing the desired compound were concentrated under reduced pressure. To the resulting crude product were added methylene chloride (5 ml) and diisopropyl ether (10 ml), followed by being left for 1 hour. A precipitated solid was collected by filtration, and dried under reduced pressure at 35° C. to afford the title compound (1.49 g) as a white solid. (Yield: 92%)

Workup

  1. customReaction
  2. additionwas added to the reaction solution
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe separated organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additioncontaining the desired compound
  8. concentrationwere concentrated under reduced pressure
  9. additionTo the resulting crude product were added methylene chloride (5 ml) and diisopropyl ether (10 ml)
  10. filtrationA precipitated solid was collected by filtration
  11. customdried under reduced pressure at 35° C.

Sources & evidence

ORD record
ord-8eda0484279f496ea7802c5a0bebc6f6
Source dataset
uspto-grants-2014_02
Patent number
US08648097B2

Reaction notes

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