Carbon Tetrachloride → Benzenemethanamine, 2,5-dichloro-

HRID 1169872Notes

Reaction equation

HRID 1169872 reaction equation
C([NH2:8])C1C=CC=CC=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[CH3:17].Br[N:19]1[C:23](=O)[CH2:22][CH2:21][C:20]1=O.C1(=O)NC(=O)C2=CC=CC=C12.[K].C(Cl)(Cl)(Cl)[Cl:39]>CN(C)C=O>[Cl:9][C:10]1[CH:11]=[CH:17][C:20]([Cl:39])=[CH:21][C:22]=1[CH2:23][NH2:19].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:11]=1[CH2:17][NH2:8]

Participants

8

Reactant 5

HCID 5943Carbon TetrachlorideHCID 7504BenzylamineHCID 67184N-bromobutanimideHCID 42009962-Chloro-5-iodotolueneHCID 24194345Phthalimide potassium salt

Product 2

HCID 457600Benzenemethanamine, 2,5-dichloro-HCID 114608822-Chloro-5-iodobenzenemethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The various benzylamine derivatives used in this study, when not commercially available, were synthesized by the methods shown in FIG. 5. 2,5-Dichlorobenzylamine 64 and 2-chloro-5-iodobenzylamine 65 were prepared from the corresponding benzyl bromides. Compound 60 was prepared from 2-chloro-5-iodotoluene by bromination with N-bromosuccinimide in CCl4. Wilson et al., J. Med. Chem 1989, 32, 1057-1062. 60 and 61 were treated with potassium phthalimide in N,N-dimethylformamide at 60° C. to obtain compounds 62 and 63 as white solids in 95% yield. Deprotection with hydrazine gave 64 and 65 in 80% yield. Treu et al., Molecules 2002, 7, 743-750.

Workup

  1. customwere synthesized by the methods

Sources & evidence

ORD record
ord-90cacdc0e5ea44a0be82d06ded280f36
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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