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1,4-Dioxane hydrochloride → (6-Phenylpyridazin-3-ylmethyl)amine hydrochloride

HRID 2359812
Notes
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Reaction equation

HRID 2359812 reaction equation
C(OC([N:8]([CH2:16][C:17]1[N:18]=[N:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:21][CH:22]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:29].O1CCOCC1>C(Cl)Cl>[ClH:29].[C:23]1([C:20]2[N:19]=[N:18][C:17]([CH2:16][NH2:8])=[CH:22][CH:21]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 667177003-[Bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine

Product 1

HCID 66717660(6-Phenylpyridazin-3-ylmethyl)amine hydrochlorideYield 119.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 3-[bis(tert-butoxycarbonyl)aminomethyl]-6-phenylpyridazine (178 mg, 0.462 mmol) obtained in Reference Example 2-(b) in methylene chloride (2.33 ml) was added a 4N hydrogen chloride/1,4-dioxane solution (2.33 ml, 9.32 mmol), followed by stirring at 30° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated under reduced pressure to afford the title compound (122 mg) substantially quantitatively as a slightly brown solid.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-165952f7bf86456f923e807326bfbd39
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08685986B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes