Benzenemethanamine, 3-chloro- → Benzenemethanamine, 3-chloro-

HRID 1801491Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.[ClH:10].[N:11]1([C:16]([NH2:18])=[NH:17])[CH:15]=[CH:14][CH:13]=[N:12]1.[CH3:19][CH2:20][N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23]>CN(C=O)C>[CH3:19][CH2:20][N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23].[ClH:1].[N:11]1([C:16]([NH2:18])=[NH:17])[CH:15]=[CH:14][CH:13]=[N:12]1.[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.[Cl-:10].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[CH2:8][NH:9][C:16]([NH2:17])=[NH2+:11]

Participants

Conditions

Temperature: 100 °C

Procedure

A 1 M solution of Hunig's Base in anhydrous DMF is prepared (Solution A). A 0.5 M solution of 1-H-pyrazole-1-carboxamidine hydrochloride is prepared using solution A. A 0.25 M solution of (3-chlorophenyl)methanamine in anhydrous DMF is prepared. A solution of (3-chlorophenyl)methanamine (800 μL, 200 mmol, 1.0 eq) is added to a solution of 1-H-pyrazole-1-carboxamidine hydrochloride (400 μL, 200 mmol, 1.0 eq) followed by addition of Hunig's Base (80 μL, 2.3 eq). The reaction mixture is heated at 100° C. for 24 hours. The solvent is removed under reduced pressure to give the crude desired product as a viscous oil. The crude product is dried by azeotoping with acetone and drying the residue under high vacuum. The crude 1-(3-chlorobenzyl)guanidinium chloride is used in the next step without any further purification.

Workup

customThe solvent is removed under reduced pressure

Sources & evidence

ORD record: ord-ff9c4825d4fb4f8cbedc279331739ee1
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349827B2

Reaction notes

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