Benzenesulfonyl chloride → HCID 5314675, compound

HRID 1019262Notes

Reaction equation

HRID 1019262 reaction equation
Cl.O.[NH:3]1[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[C:17]1([S:23](Cl)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([S:23]([N:3]2[CH2:8][CH2:7][C:6](=[O:9])[CH2:5][CH2:4]2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 2723901Piperonylamine

Product 1

HCID 5314675HCID 5314675, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-piperidone monohydrate hydrochloride (4.59 g, 30 mmol), triethylamine (12.5 ml, 90 mmol) in CH2Cl2 (50 ml) was added benzenesulfonyl chloride (5.30 g, 30 mmol). The mixture was stirred at 25° C. for 16 h. After evaporation of solvents, the residue was triturated with water (100 ml), filtered, and further purified by recrystallization from hexanes/CH2Cl2 (3:1) to afford the desired ketone (5.97 g, 83%) as a colorless solid. mp 116-118° C.; 1H NMR (500 MHz, CDCl3) δ2.54 (t, J=6.4Hz, 4H), 3.41(t, J=6.4Hz, 4H), 7.58 (d, J =7.8 Hz, 2H), 7.63 (t, J=7.0 Hz, 1H), 7.81 (d, J=7.8 Hz, 2H).

Workup

  1. customAfter evaporation of solvents
  2. customthe residue was triturated with water (100 ml)
  3. filtrationfiltered
  4. customfurther purified by recrystallization from hexanes/CH2Cl2 (3:1)

Sources & evidence

ORD record
ord-8a7b44dbc01f4e71822a8133f3f8f721
Source dataset
uspto-grants-2002_11
Patent number
US06486199B1

Reaction notes

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