4-Methylmorpholine → Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amide

HRID 229782

Reaction equation

HRID 229782 reaction equation
[CH2:1]([NH:4][CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH2:9])[CH:2]=[CH2:3].CN1CCOCC1.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[CH2:1]([N:4]([CH2:5][CH:6]([CH3:10])[CH2:7][CH:8]=[CH2:9])[S:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=1)(=[O:26])=[O:25])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 11378535Allyl-(2-methyl-pent-4-enyl)-amine

Product 1

HCID 11565389Pyridine-2-sulfonic acid allyl-(2-methyl-pent-4enyl)-amideYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Allyl-(2-methyl-pent-4-enyl)-amine (1.0 g, 7.2 mmol) and NMM (1.7 g, 17.2 mmol) were mixed in 30 ml CH2Cl2.2-pyridinesulphonyl chloride (1.53 g, 8.6 mmol) was added slowly to the solution while it was cooled in an ice-water bath. After addition, the reaction mixture was stirred at RT overnight. The reaction mixture was washed with 10% NaHCO3 and the brine, then was purified by column chromatography to give the title compound as a colorless oil (1.2 g, 60% yield): MS (M+H+) 281.2; 1H-NMR (400 Hz, CDCl3): d=8.70(d, 1H), 8.0-7.75(m, 2H), 7.5 (m, 1H) 5.80-5.60(m, 2H), 5.15-4.92(m, 4H), 4.00-3.90(m, 2H), 3.20-3.06(m, 2H), 2.15(m, 1H), 1.85(m, 2H), 0.89(d, 3H)

Workup

  1. temperaturewas cooled in an ice-water bath
  2. additionAfter addition
  3. washThe reaction mixture was washed with 10% NaHCO3
  4. customthe brine, then was purified by column chromatography

Sources & evidence

ORD record
ord-3a35586a6d834ac8bf154c8f82a5b12d
Source dataset
uspto-grants-2009_07
Patent number
US07563784B2

Linked notes

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