Hydrogen Bromide → (S)-1-bromomethyl-2-(3H-imidazol-4-yl)-ethylamine

HRID 2380817Notes

Reaction equation

HRID 2380817 reaction equation
[NH2:1][C@H:2]([CH2:9]O)[CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.[BrH:11]>C(O)(=O)C.C(O)C>[Br:11][CH2:9][C@@H:2]([NH2:1])[CH2:3][C:4]1[NH:8][CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 178418337HCID 178418337, compound

Product 1

HCID 69071454(S)-1-bromomethyl-2-(3H-imidazol-4-yl)-ethylamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

900 mg (S)-histidinol (×2HCl) are dissolved in 20 mL HBr in acetic acid (32%) and heated to 110° C. in the microwave for 6 h. The solvent is eliminated in vacuo, the residue is dissolved in ethanol and again freed from the solvent in vacuo. This crude product is used in the next reaction step without further purification.

Sources & evidence

ORD record
ord-f31c1ac2e5a84deb8146f72f9c708390
Source dataset
uspto-grants-2012_09
Patent number
US08258129B2

Reaction notes

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