p-Bromobenzenesulfonyl chloride → HCID 1219636, compound

HRID 1936566Notes

Reaction equation

HRID 1936566 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.[NH:12]1[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 1219636HCID 1219636, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromophenyl sulphonyl chloride (53.76 g) in dichloromethane (700 ml) was added to a stirred solution of ethyl piperidine-4-carboxylate (32.97 g) in dichloromethane (500 ml) containing triethylamine (36 ml) at 0° C. and under argon over 0.75 hours. The reaction was stirred for 18 hours. The reaction mixture was washed with water (2×500 ml), saturated brine (1×500 ml), dried and evaporated. The residual solid was triturated in isohexane (500 ml) for 1 hour, collected by filtration and dried to give, as a colourless solid, ethyl 1-(4-bromophenylsulphonyl)piperidine-4-carboxylate (79 g); mp 132-3° C.; NMR (CDCl3): 1.21(t, 3H), 1.70-1.90(m, 2H), 1.90-2.05(m, 2H), 2.18-2.33(m, 1H), 2.45-2.60(m, 2H), 3.53-3.67(m, 2H), 4.10(q, 2H), 7.55-7.70(m, 4H); EI-MS m/z 376 (M+H).

Workup

  1. washThe reaction mixture was washed with water (2×500 ml), saturated brine (1×500 ml)
  2. customdried
  3. customevaporated
  4. customThe residual solid was triturated in isohexane (500 ml) for 1 hour
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-cb45392aa6b64c2eb4a9cc8857d1fb2b
Source dataset
uspto-grants-2002_05
Patent number
US06391880B1

Reaction notes

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