Piperidine → HCID 19064525, compound

HRID 481982Notes

Reaction equation

HRID 481982 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[C:7]([CH:10]3[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]3)[C:6]=2[CH:17]=1.[CH3:18][S:19]([Cl:22])(=[O:21])=[O:20].N1CCCCC1>ClCCl>[ClH:22].[CH3:16][N:13]1[CH2:12][CH2:11][CH:10]([C:7]2[C:6]3[CH:17]=[C:2]([NH:1][S:19]([CH3:18])(=[O:21])=[O:20])[CH:3]=[CH:4][C:5]=3[O:9][CH:8]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 31297Methanesulfonyl chlorideHCID 19064653HCID 19064653, compound

Product 1

HCID 19064525HCID 19064525, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.018 gm (0.07 mMol) 5-amino-3-(1-methylpiperidin-4-yl)benzofuran, 16.2 μL (0.21 mMol) methanesulfonyl chloride, and 0.100 gm (4 equivalents) of polymer bound piperidine in 1.5 mL dichloromethane. The reaction mixture was agitated for 24 hours at room temperature. The reaction mixture was then loaded onto a VARIAN BOND ELUT SCX™ (Varian, Harbor City, Calif., U.S.A.) ion exchange column, eluting first with several volumes of methanol and then with 10 mL 2M ammonia in methanol. Fractions containing product were combined and concentrated under reduced pressure. The residue was dissolved in methanolic hydrogen chloride and then the solvent removed. This step was repeated three times to provide 0.0061 gm of the title compound.

Workup

  1. washeluting first with several volumes of methanol
  2. additionFractions containing product
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in methanolic hydrogen chloride
  5. customthe solvent removed

Sources & evidence

ORD record
ord-2cc36d70829345f88a566509130aa79a
Source dataset
uspto-grants-1998_08
Patent number
US05792763

Reaction notes

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