4-Nitrobenzenesulfonyl chloride → HCID 2242107, compound

HRID 1418377Notes

Reaction equation

HRID 1418377 reaction equation
[CH2:1]1[O:10][C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[O:3][CH2:2]1.C(N(CC)CC)C.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]>C(OCC)(=O)C>[CH2:1]1[O:10][C:4]2([CH2:9][CH2:8][N:7]([S:27]([C:24]3[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:26][CH:25]=3)(=[O:28])=[O:29])[CH2:6][CH2:5]2)[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 2242107HCID 2242107, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-piperidone ethylene ketal (1.28 ml, 10 mmol) and triethylamine (1.4 ml, 10 mmol) in ethyl acetate (20 ml) was treated with a dropwise addition of 4-nitro-phenylsulphonyl chloride (1.4 ml, 10 mmol) in ethyl acetate (20 ml) and stirred at room temperature for 2 h. The mixture was washed with water, dilute HCl, saturated sodium bicarbonate solution and brine, dried over sodium sulphate and evaporated to leave the title compound as a solid (2.8 g), MS (+EI) 328 (M+), 1H NMR (CDCl3) 8.38 (2H, d, J 8.8 Hz), 7.96 (2H, d, J 8.8 Hz), 3.90 (4H, s), 3.22 (4H, t, J 5.7 Hz), 1.80 (4H, t, J 5.7 Hz).

Workup

  1. washThe mixture was washed with water, dilute HCl, saturated sodium bicarbonate solution and brine
  2. dry with materialdried over sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-1c99faa8105f459dbf28b5547b4cee9d
Source dataset
uspto-grants-1999_03
Patent number
US05883102

Reaction notes

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