1,1'-Carbonyldiimidazole → 3-[(3-Chlorophenyl)sulfonyl]-N-[2-(dimethylamino)ethyl]-1-piperidinecarboxamide Monohydrochloride

HRID 236113Notes

Reaction equation

HRID 236113 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13]NN(CC)NC.[Cl:20][C:21]1[CH:22]=[C:23]([S:27]([CH:30]2[CH2:35][CH2:34][CH2:33][NH:32][CH2:31]2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1>O1CCCC1.C(Cl)Cl>[ClH:20].[Cl:20][C:21]1[CH:22]=[C:23]([S:27]([CH:30]2[CH2:35][CH2:34][CH2:33][N:32]([C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:13])=[O:2])[CH2:31]2)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 136079853-[(3-Chlorophenyl)sulfonyl]piperidineHCID 57041336N,N-Dimethylaminoethylamine

Product 1

HCID 202178793-[(3-Chlorophenyl)sulfonyl]-N-[2-(dimethylamino)ethyl]-1-piperidinecarboxamide Monohydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.57 g (0.022 mole) of 1,1'-carbonyldiimidazole and 1.78 g (0.020 mole) of N,N-dimethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 4.63 g (0.0179 mole) of 3-[(3-chlorophenyl)sulfonyl]piperidine (free base) in 100 ml of tetrahydrofuran was added and the mixture was refluxed for 22 hr. The solvent was removed in vacuo to give an oil. The oil was dissolved in methylene chloride and the solution was extracted with 6 portions of water, the water washes being discarded. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo to give an oil, the free base of the title compound. The free base was converted to the hydrochloride salt as in Example 14 to give 3.39 g (46.2%) of white crystals, m.p. 181°-183° C. with decomposition.

Workup

  1. temperaturethe mixture was refluxed for 22 hr
  2. customThe solvent was removed in vacuo
  3. customto give an oil
  4. extractionthe solution was extracted with 6 portions of water
  5. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-2a535a938163465b8f193c512532becd
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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