Benzylamine → 4-[3-(N-benzylamino)propylthio)pyridine

HRID 274674Notes

Reaction equation

HRID 274674 reaction equation
O[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH2:24]([NH:31][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190791344-(3-Hydroxypropylthio)pyridine

Product 1

HCID 190791904-[3-(N-benzylamino)propylthio)pyridineYield 16.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 150 ml of methylene chloride were dissolved 5.22 g (30.8 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.16 ml (37.0 mmol) of triethylamine, methanesulfonyl chloride [2.86 ml (37.0 mmol)] was added, and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried. Then the solvent was distilled off. 2.62 ml (24.0 mmol) of benzylamine was added to the residue, and the mixture was heated at 80° C. for 3 hours. After cooling, the mixture was purified by column chromatography (eluent: chloroform/methanol=25:1) to obtain 1.0 g of the desired compound (yield: 16.1% yellow oil)

Workup

  1. additionwas added
  2. washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
  3. customdried
  4. distillationThen the solvent was distilled off
  5. temperaturethe mixture was heated at 80° C. for 3 hours
  6. temperatureAfter cooling
  7. customthe mixture was purified by column chromatography (eluent: chloroform/methanol=25:1)

Sources & evidence

ORD record
ord-f43f03d9d5dc489da2499ddb14600e96
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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