1-Naphthalenesulfonyl chloride → HCID 3759656, compound

HRID 2356215Notes

Reaction equation

HRID 2356215 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[C:10]1([S:20](Cl)(=[O:22])=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[C:10]1([S:20]([N:7]2[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]2)(=[O:22])=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 665601-Naphthalenesulfonyl chlorideHCID 837951-Acetylpiperazine

Product 1

HCID 3759656HCID 3759656, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

1-Acetylpiperazine (0.500 g, 3.9 mmol), 1-naphthalenesulfonyl chloride (0.884 g, 3.9 mmol) and DMAP (0.095 g, 0.70 mmol) were dissolved in pyridine (6 mL). After stirring overnight, the reaction mixture was concentrated in vacuo, and quenched with an ice cold solution of 1.0 M HCl (15 mL). The resulting precipitate was filtered and rinsed with water. Trituration with ether followed by filtration provided the 1.06 g (85%) of the title compound as a white solid. 1H NMR (400 MHz, Chloroform-d) δ, ppm: 2.00 (s, 3 H), 3.12-3.21 (m, 4 H), 3.45-3.54 (m, 2 H), 3.57-3.67 (m, 2 H), 7.56-7.67 (m, 3 H), 7.94 (d, J=7.58 Hz, 1 H), 8.10 (d, J=8.08 Hz, 1 H), 8.20 (d, J=7.58 Hz, 1 H), 8.73 (d, J=9.09 Hz, 1 H); ESI-MS: m/z 319.4 (M+H)+.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customquenched with an ice cold solution of 1.0 M HCl (15 mL)
  3. filtrationThe resulting precipitate was filtered
  4. washrinsed with water
  5. filtrationTrituration with ether followed by filtration

Sources & evidence

ORD record
ord-dfa18aae9e4f42b79668c91225edcd20
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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