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Hydrochloric Acid → (1H-imidazol-4-yl)methanamine dihydrochloride

HRID 333442
Notes
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Reaction equation

HRID 333442 reaction equation
N1([N:7]=[CH:8][C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)CCCCC1.C1COCC1.C(O)C.[ClH:41]>C(OCC)(=O)C.[Pd]>[ClH:41].[ClH:41].[NH:12]1[CH:13]=[C:9]([CH2:8][NH2:7])[N:10]=[CH:11]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8028TetrahydrofuranHCID 66987946Piperidin-1-yl-(1-trityl-1H-imidazol-4-yl-methylene)amine

Product 1

HCID 178478688(1H-imidazol-4-yl)methanamine dihydrochlorideYield 29%

Reagents, catalysts & solvents 2

HCID 23938
Palladium
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution containing 450 mg of piperidin-1-yl-(1-trityl-1H-imidazol-4-yl-methylene)amine in 3.5 mL of 3N hydrogen chloride in ethyl acetate are added 90 mg of 10% Pd/C, 0.5 mL of THF and 0.9 mL of ethanol. The reaction medium is placed under a hydrogen pressure of 6 bar and heated at 80° C. for 3 hours. After filtering off the catalyst and evaporating off the solvents, the crude product obtained is chromatographed on silica gel (eluent: 6/4 DCM/MeOH). 50 mg of C-(1H-imidazol-4-yl)methylamine dihydrochloride in the form of a white powder are obtained in a yield of 29%.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customevaporating off the solvents
  3. customthe crude product obtained
  4. customis chromatographed on silica gel (eluent: 6/4 DCM/MeOH)

Sources & evidence

ORD record
ord-32f171c68d024b799c116604e161a63e
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877968B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes