HCID 145855263, compound → tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate

HRID 1243353Notes

Reaction equation

HRID 1243353 reaction equation
C([NH:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[NH:21])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:8][CH:7]=1)C=C>C(#N)C.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:17]([O:16][C:14]([NH:13][C:12]([C:9]1[CH:8]=[CH:7][C:6]([CH2:5][NH2:4])=[CH:11][CH:10]=1)=[NH:21])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 1

HCID 145855263HCID 145855263, compound

Product 1

HCID 145832046tert-butyl N-[4-(aminomethyl)benzenecarboximidoyl]carbamate

Reagents, catalysts & solvents 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The N-allyl-4-(t-butoxycarbonylamidino)benzylamine (3.97 mmoles, 1.15 g) and chlorotris(triphenylphosphine)-rhodium(I) (0.21 mmoles, 195 mg) was stirred in acetonitrile/water (84:16, 92 mL) under nitrogen. The mixture was refluxed for 3 hr and allowed to cool to room temperature. Then the mixture was filtered through a pad of celite and the solvent removed in vacuo. The residue was dried on a high vacuum pump to yield an orange glassy product 4-(t-Butoxycarbonylamidino)benzylamine product was verified by HPLC/MS and used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 3 hr
  2. filtrationThen the mixture was filtered through a pad of celite
  3. customthe solvent removed in vacuo
  4. customThe residue was dried on a high vacuum pump

Sources & evidence

ORD record
ord-a24e33438ad04c8d9bc8239ace0a950c
Source dataset
uspto-grants-2006_10
Patent number
US07119094B1

Reaction notes

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