p-Bromobenzenesulfonyl chloride → HCID 1219636, compound

HRID 2289536Notes

Reaction equation

HRID 2289536 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:20]2[CH2:21][CH2:22][CH:17]([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH2:18][CH2:19]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 1219636HCID 1219636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromophenylsulphonyl chloride (7.68 g) in dichloromethane (100 ml) was added dropwise over a period of 30 minutes to a solution of 4-(ethoxycarbonyl)piperidine (4.71 g) in dichloromethane (50 ml) at 0° C. and under argon. The mixture was stirred overnight during which time it was allowed to warm to room temperature. The organic phase was washed with water, brine, dried and evaporated to give a solid. This solid was triturated in petroleum ether (bp 40-60° C.) to give 1-(4-bromophenylsulphonyl)-4-(ethoxycarbonyl)piperidine (l0.05 g), m.p. 137-133° C.

Workup

  1. washThe organic phase was washed with water, brine
  2. customdried
  3. customevaporated
  4. customto give a solid
  5. customThis solid was triturated in petroleum ether (bp 40-60° C.)

Sources & evidence

ORD record
ord-76173876f7274bdebbd9fbbde9d2aee9
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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