Dimethylamine → HCID 58998500, compound

HRID 1430555Notes

Reaction equation

HRID 1430555 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-2c2c0240ad514fdab87f03206f739a14
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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