Water → HCID 53756535, compound

HRID 2084919Notes

Reaction equation

HRID 2084919 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[C:21]#[C:22][CH3:23].O>N1C=CC=CC=1>[CH2:18]([O:17][C:15]([CH:11]1[CH2:10][N:9]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])[CH2:14][CH2:13][N:12]1[S:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:20][C:21]#[C:22][CH3:23])=[CH:30][CH:29]=1)(=[O:33])=[O:32])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 22644747HCID 22644747, compound

Product 1

HCID 53756535HCID 53756535, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The ethyl 4-(4-morpholinylcarbonyl)-2-piperazinecarboxylate (0.41 g, 1.55 mmol) was dissolved in pyridine (1.44 mL). To this solution was added a solution of 4-but-2-ynyloxy-benzenesulfonyl chloride (0.38 g, 1.55 mmol) in pyridine (1 mL). The reaction was stirred overnight and then poured into water. The mixture was extracted three times with chloroform. The organics were combined, washed with 10% HCl, twice with water, then brine and dried over Na2SO4. The solution was filtered and concentrated in vacuo to provide 0.6 g (81%) of 1-(4-but-2-ynyloxy-benzenesulfonyl)-4-(morpholine-4-carbonyl)-piperazine-2-carboxylic acid ethyl ester as a gold oil. Electrospray Mass Spec 480.2 (M+H)+.

Workup

  1. extractionThe mixture was extracted three times with chloroform
  2. washwashed with 10% HCl, twice with water
  3. dry with materialbrine and dried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4e31c64ef9c46e5a22d030cfceca231
Source dataset
uspto-grants-2004_04
Patent number
US06716833B2

Reaction notes

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