Dimethylformamide → HCID 19735247, compound

HRID 326551Notes

Reaction equation

HRID 326551 reaction equation
S([C:9]1[CH:15]=[CH:14][C:12]([CH3:13])=[CH:11][CH:10]=1)(OCCC#C)(=O)=O.N1C=[CH:20][CH:19]=[CH:18][C:17]=1[N:22]1CC[NH:25][CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+].C[N:34](C)C=O>>[N:34]1[CH:11]=[CH:10][CH:9]=[CH:15][C:14]=1[CH:12]1[CH2:13][NH:25][CH2:24][CH2:23][N:22]1[CH2:17][CH2:18][C:19]#[CH:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 944591-(2-Pyridyl)piperazineHCID 2720203-Butynyl p-toluenesulfonateHCID 516892Sodium Bicarbonate

Product 1

HCID 19735247HCID 19735247, compound

Procedure

A solution of 3-butynyl tosylate (25.0 g, 0.11 mol), 1-(2-pyridinyl)piperazine (12.1 g, 0.074 mol), and sodium bicarbonate (6.9 g, 0.082 mol) in 200 mL of dimethylformamide is heated at 80° C. for 18 hours. The solvent is removed under reduced pressure, and the residue is partitioned between 200 mL of dichloromethane and 200 mL of water. The aqueous layer is extracted with 100 mL of dichloromethane and the combined organic layers are dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane) to give the title compound as a white solid; mp 57°-58° C.

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between 200 mL of dichloromethane and 200 mL of water
  3. extractionThe aqueous layer is extracted with 100 mL of dichloromethane
  4. dry with materialthe combined organic layers are dried (sodium sulfate)
  5. customthe solvent is removed in vacuo
  6. customThe residue is chromatographed (silica gel, 25% ethyl acetate/75% hexane)

Sources & evidence

ORD record
ord-f0cab2c702504be88a226eb5338b48c5
Source dataset
uspto-grants-1993_12
Patent number
US05270312

Reaction notes

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