Dimethylamine → Methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate

HRID 1426292Notes

Reaction equation

HRID 1426292 reaction equation
[CH3:1][NH:2][CH3:3].C1COCC1.Br[CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15]>C(Cl)Cl>[CH3:1][N:2]([CH2:10][C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([F:21])[CH:20]=1)[C:14]([O:16][CH3:17])=[O:15])[CH3:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 58938186methyl 3-(bromomethyl)-5-fluorobenzoate

Product 1

HCID 69672877Methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.0M dimethylamine in THF (3.24 mL, 6.48 mmol) was added methylene chloride (2 mL) and methyl 3-(bromomethyl)-5-fluorobenzoate (0.200 g, 0.810 mmol from Step 2). The reaction was heated in a sealed reaction vessel in an oil bath held at 60° C. for 2 hours. Solvent and excess reagent were removed in vacuo and the residue was subjected to flash chromatography, eluting with a gradient from 0-20% MeOH in DCM containing some NH4OH (50 mg, 29%). 1H NMR (300 MHz, CDCl3): δ 7.80-7.77 (m, 1H), 7.62 (ddd, 1H), 7.29 (ddd, 1H), 3.90 (s, 3H), 3.53 (s, 2H), 2.29 (s, 6H); 19F NMR (282 MHz, CDCl3): δ−113.10 (t, 1F); LCMS (M+H)+: 212.1.

Workup

  1. temperatureThe reaction was heated in a sealed reaction vessel in an oil bath
  2. customSolvent and excess reagent were removed in vacuo
  3. washeluting with a gradient from 0-20% MeOH in DCM containing some NH4OH (50 mg, 29%)

Sources & evidence

ORD record
ord-b8af74c104764323ba08d83231fb6904
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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