Water → HCID 43394298, compound

HRID 2281430Notes

Reaction equation

HRID 2281430 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.O>C(Cl)Cl.CCOC(C)=O>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:18]2[CH2:19][CH2:20][CH:15]([OH:14])[CH2:16][CH2:17]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 79341Piperidin-4-ol

Product 1

HCID 43394298HCID 43394298, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-nitrobenzenesulfonyl chloride (512 mg, 2.31 mmol) in CH2Cl2 (8 mL) at room temperature, 4-hydroxypiperidine (404 mg, 4.00 mmol) was added. Triethylamine (0.400 mL, 2.88 mmol) was also added. The mixture was stirred at room temperature overnight. Water and EtOAc were added. The organic phase was separated, washed with 1N HCl, dried over Na2SO4, concentrated in vacuo to give 1-(4-nitrophenylsulfonyl)piperidin-4-ol as a solid (559 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 1N HCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d7d3694fd7f410d83c1ad900975bb2b
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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