Dimethylamine → HCID 58998500, compound

HRID 1257265Notes

Reaction equation

HRID 1257265 reaction equation
C[CH2:2][N:3]([CH:7]([CH3:9])C)[CH:4](C)C.CNC.BrC[C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=C[C:16]=1[F:24].CCOC(C)=O>C1COCC1>[F:24][C:16]1[CH:15]=[CH:20][C:19]([N+:21]([O-:23])=[O:22])=[CH:18][C:9]=1[CH2:7][N:3]([CH3:2])[CH3:4]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 103539672-(Bromomethyl)-1-fluoro-4-nitrobenzene

Product 1

HCID 58998500HCID 58998500, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −20° C. solution of DIEA (771 mg, 5.97 mmol) and dimethylamine (2.0M in THF, 1.94 mL, 3.88 mmol) in THF (5 mL) was treated drop-wise with a solution of 2-(bromomethyl)-1-fluoro-4-nitrobenzene (698 mg 2.98 mmol) in THF (5 mL) and stirred at RT overnight as the cooling bath expired. The mixture was treated with EtOAc, washed with water, then brine, dried over Na2SO4 and concentrated to dryness to afford 1-(2-fluoro-5-nitrophenyl)-N,N-dimethylmethanamine (494 mg, 84% yield). MS (ESI) m/z: 199.1 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialbrine, dried over Na2SO4
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-92c6f74a4e744c03b2189d9e97e071bf
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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