Triethylamine → 4-(N-cyclohexylcarbonylaminomethyl)-1-(1-naphthylsulfonyl)piperidine

HRID 2110833Notes

Reaction equation

HRID 2110833 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([S:9]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH:29]1([C:35](Cl)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>ClCCl>[CH:29]1([C:35]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([S:9]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)(=[O:11])=[O:10])[CH2:5][CH2:4]2)=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 688620304-Aminomethyl-1-(1-naphthylsulfonyl)piperidine

Product 1

HCID 688599634-(N-cyclohexylcarbonylaminomethyl)-1-(1-naphthylsulfonyl)piperidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminomethyl-1-(1-naphthylsulfonyl)piperidine (608 mg, 2.0 mmol) and triethylamine (303 mg, 3.0 mmol) in dichloromethane (30 mL) stirring at room temperature under argon, was added cyclohexanecarbonyl chloride (325 mg, 2.2 mmol) in a single portion. After 2 h the solvent was evaporated under vacuum, and the residue was slurried with diethyl ether and filtered. The filtrate was evaporated, and purification by column chromatography (silica gel, ethyl acetate in hexane) provided 4-(N-cyclohexylcarbonylaminomethyl)-1-(1-naphthylsulfonyl)piperidine (793 mg, 96% yield) as a gum.

Workup

  1. customAfter 2 h the solvent was evaporated under vacuum
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. custompurification by column chromatography (silica gel, ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f643e47e2717433083b62cb0772d15a6
Source dataset
uspto-grants-2009_04
Patent number
US07517991B2

Reaction notes

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