Hydrochloric Acid → 2-amino-3-[3-(3-cyanophenoxy)phenyl]-N,N-dimethylpropanamide HCl salt

HRID 449510Notes

Reaction equation

HRID 449510 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[O:6][C:7]1[CH:8]=[C:9]([CH2:13][CH:14]([NH:20]C(=O)OC(C)(C)C)[C:15]([N:17]([CH3:19])[CH3:18])=[O:16])[CH:10]=[CH:11][CH:12]=1)#[N:2].[ClH:31]>O1CCOCC1>[ClH:31].[NH2:20][CH:14]([CH2:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:28]=[CH:29][CH:30]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH:8]=1)[C:15]([N:17]([CH3:19])[CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59496582Tert-butyl 3-(3-(3-cyanophenoxy)phenyl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 675415352-amino-3-[3-(3-cyanophenoxy)phenyl]-N,N-dimethylpropanamide HCl salt

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 3-(3-(3-cyanophenoxy)phenyl)-1-(dimethylamino)-1-oxopropan-2-ylcarbamate (0.045 g crude) was taken up in 4 M HCl in dioxane 2 ml and stirred at r.t. for 2 h. The reaction was complete, concentrated under reduced pressure in vacuo. The residue was taken up in acetonitrile and reconcentrated under reduced pressure two times to give crude 2-amino-3-[3-(3-cyanophenoxy)phenyl]-N,N-dimethylpropanamide-HCl salt (0.045 g) as a semisolid residue which was directly used in next step reaction without further purification. Analytical LCMS (M+H)+: m/z=310.0

Workup

  1. concentrationconcentrated under reduced pressure in vacuo

Sources & evidence

ORD record
ord-c100df05a2d84ccda712c0c8b16f2924
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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