1,4-Dioxane hydrochloride → HCID 10287586, compound

HRID 2109997Notes

Reaction equation

HRID 2109997 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=2[N:10]=[C:9]1[NH:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[CH2:22][CH2:21]1)=O)(C)(C)C.O1CCOCC1.Cl>CO>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[CH2:26][N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][NH:18][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH2:17])[C:11]=3[N:10]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69070206HCID 69070206, compound

Product 1

HCID 10287586HCID 10287586, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

After dissolving 4-amino-2-{[1-(3,4-dichloro-benzyl)-piperidin-4-ylmethyl]-amino}-benzimidazole-1-carboxylic acid tert-butyl ester (10 mg, 0.02 mmol) in methanol (1 ml), a 4N hydrogen chloride-1,4-dioxane solution (1 ml) was added and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was passed through SCX (Bond Elute SCX500MG), the SCX was washed with methanol, and then elution was performed with a 2N ammonia-methanol solution. The solvent was distilled off under reduced pressure to obtain N2-[1-(3,4-dichlorobenzyl)-piperidin-4-ylmethyl]-1H-benzimidazole-2,4-diamine. The compound was identified by LC-MS.

Workup

  1. washThe reaction mixture was passed through SCX (Bond Elute SCX500MG)
  2. washthe SCX was washed with methanol
  3. washelution
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b85ee370d2884472a32648c09c6222e1
Source dataset
uspto-grants-2009_04
Patent number
US07517875B2

Reaction notes

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