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

HRID 333442Notes

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

Participants

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

filtrationAfter filtering off the catalyst
customevaporating off the solvents
customthe crude product obtained
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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