1,4-Dioxane hydrochloride → N,N-bis(1H-imidazol-2-ylmethyl)-N'-(piperidin-4-ylmethyl)urea

HRID 1920129Notes

Reaction equation

HRID 1920129 reaction equation
CN(C)S([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:30][C:31]1[N:32](S(N(C)C)(=O)=O)[CH:33]=[CH:34][N:35]=1)[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1)=[O:14])(=O)=O.Cl.O1CCOCC1>>[NH:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:30][C:31]1[NH:32][CH:33]=[CH:34][N:35]=1)[C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:14]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67500244tert-butyl 4-[({[bis({1-[(dimethylamino)sulfonyl]-1H-imidazol-2-yl)methyl]amino}carbonyl)amino]methyl}piperidine-1-carboxylate

Product 1

HCID 67502645N,N-bis(1H-imidazol-2-ylmethyl)-N'-(piperidin-4-ylmethyl)urea

Conditions

Temperature
60 °C

Procedure

To the compound (3.00 g) obtained in Example 9, 4N hydrogen chloride/dioxane (15 mL) was added. The reaction solution was stirred at 60° C. for 15 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved in methanol (20 mL) and a carbonate resin (trade name: MP-Carbonate, manufactured by Argonaut Co., product number: 800267, 10 g) was added, followed by stirring at room temperature for 3 hours. After the resin was removed by filtration, the filtrate was concentrated under reduced pressure. The title compound was obtained without purifying the residue.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol (20 mL)
  3. additiona carbonate resin (trade name: MP-Carbonate, manufactured by Argonaut Co., product number: 800267, 10 g) was added
  4. stirringby stirring at room temperature for 3 hours
  5. customAfter the resin was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a7d058d7e1cc422cbc3e29fa29c8d22c
Source dataset
uspto-grants-2012_05
Patent number
US08168783B2

Reaction notes

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