Triethylamine → Methanesulfonic acid 2-{[3-(4-cyanophenyl)propyl]methanesulfonylamino}ethyl ester

HRID 899117Notes

Reaction equation

HRID 899117 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C(Cl)Cl>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([CH2:7][CH2:6][CH2:5][N:4]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:3][CH2:2][O:1][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:9][CH:10]=1)#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 690715794-[3-(2-Hydroxyethylamino)propyl]benzonitrile

Product 1

HCID 86616240Methanesulfonic acid 2-{[3-(4-cyanophenyl)propyl]methanesulfonylamino}ethyl esterYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[3-(2-hydroxyethylamino)propyl]benzonitrile (4 g, 0.0196 mol; see step (v) above) in dry DCM (80 mL) were added, at 0-5° C., triethylamine (5.9 g, 0.0588 mol) and mesyl chloride (5.6 g, 0.049 mol). The resulting mixture was then stirred at room temperature for 30 min, after which the reaction was quenched by addition of water (50 mL). The resulting aqueous layer was extracted with DCM (2×50 mL) and the combined organic layers were washed with brine. Solvent was removed under reduced pressure and the crude product was recrystallised from methanol to yield 4.2 g (62%) of the title compound as a white solid.

Workup

  1. customafter which the reaction was quenched by addition of water (50 mL)
  2. extractionThe resulting aqueous layer was extracted with DCM (2×50 mL)
  3. washthe combined organic layers were washed with brine
  4. customSolvent was removed under reduced pressure
  5. customthe crude product was recrystallised from methanol

Sources & evidence

ORD record
ord-a3ef3cfe6df7420396bb1662ce221852
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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