HCID 178418361, compound → 1-(5-chloro-1H-1,3-benzodiazol-2-yl)ethan-1-amine

HRID 2053751Notes

Reaction equation

HRID 2053751 reaction equation
C(OC([NH:11][CH:12]([C:14]1[NH:18][C:17]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:16]=2[N:15]=1)[CH3:13])=O)C1C=CC=CC=1.[H][H]>CO.C(Cl)Cl.[Pd]>[Cl:23][C:21]1[CH:20]=[CH:19][C:17]2[N:18]=[C:14]([CH:12]([NH2:11])[CH3:13])[NH:15][C:16]=2[CH:22]=1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178465383HCID 178465383, compound

Product 1

HCID 242525581-(5-chloro-1H-1,3-benzodiazol-2-yl)ethan-1-amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

5.00 g (contaminated) of rac.-N-benzyloxycarbonyl-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine is dissolved in a mixture of 100 mL of methanol and 40 mL methylene chloride, combined with 1.0 g palladium on charcoal, and hydrogenated for 1 hour at 3.4 bar hydrogen pressure. The solvents are distilled off and the crude product is purified by chromatography with silica gel (eluent: methylene chloride/ethanol=95:5+0.2% ammonia). Yield: 1.08 g (25% over 3 steps); Rf value: 0.37 (silica gel; dichloromethane/ethanol=4:1+2% ammonia); C9H10ClN3 (195.65); mass spectrum: (M+H)+=196/198 (chlorine isotope).

Workup

  1. distillationThe solvents are distilled off
  2. customthe crude product is purified by chromatography with silica gel (eluent: methylene chloride/ethanol=95:5+0.2% ammonia)

Sources & evidence

ORD record
ord-944afc9223514085821146f234ec9e69
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

Loading…