Dimethylamine, hydrochloride → HCID 58998500, compound

HRID 1593065Notes

Reaction equation

HRID 1593065 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[F:12].Cl.[CH3:14][NH:15][CH3:16].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1>[F:12][C:4]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=1[CH2:2][N:15]([CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 10796Cesium carbonateHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 58998500HCID 58998500, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 2-bromomethyl-1-fluoro-4-nitro-benzene (131 mg, 0.56 mmol), which was generated in Example 64) and dimethylamine hydrochloride (44 mg, 0.54 mmol) in 4 mL dioxane, was added cesium carbonate (546 mg, 1.68 mmol). The mixture was heated to 70° C. under argon for 12 hours. Work up and RP prep HPLC to give (2-fluoro-5-nitro-benzyl)-dimethyl-amine.

Sources & evidence

ORD record
ord-1fa09a302b46437a93dff3065cabf853
Source dataset
uspto-grants-2007_11
Patent number
US07294635B2

Reaction notes

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