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

HRID 1981811Notes

Reaction equation

HRID 1981811 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-933efc9e5c2b49428fa23841fccc91ed
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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