Dimethylamine → (5-Dimethylaminomethyl-benzofuran-3-yl)-acetic acid methyl ester

HRID 402907Notes

Reaction equation

HRID 402907 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([CH2:14]Br)[CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1.[CH3:17][NH:18][CH3:19]>C1COCC1.C(O)C>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:9]2[CH:10]=[C:11]([CH2:14][N:18]([CH3:19])[CH3:17])[CH:12]=[CH:13][C:8]=2[O:7][CH:6]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 59192023(5-Bromomethyl-benzofuran-3-yl)-acetic acid methyl ester

Product 1

HCID 59192009(5-Dimethylaminomethyl-benzofuran-3-yl)-acetic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-bromomethyl-benzofuran-3-yl)-acetic acid methyl ester (198 mg, 0.70 mmol) in THF (4.0 mL) is added a 5.6 M solution of dimethylamine in ethanol (1.0 mL). The resulting reaction mixture is stirred for 2 h at room temperature, filtered through a microfilter (25 μm) and the filtrate concentrated at reduced pressure to afford the title compound as a yellow oil (170 mg, 0.69 mmol, 98%). 1H NMR (400 MHz, CDCl3, 298 K): δ=7.56 (s, 1H), 7.45 (s, 1H), 7.36 (d, J=8.6 Hz, 1H), 7.23 (d, J=8.6 Hz, 1H), 3.66 (s, 3H), 3.64 (s, 2H), 3.52 (s, 2H), 2.24 (s, 3H). MS (ES+): 248 (M(C14H17NO3)+H)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered through a microfilter (25 μm)
  3. concentrationthe filtrate concentrated at reduced pressure

Sources & evidence

ORD record
ord-ce77b5b7da3c4b418e78fe5ff4c99dc5
Source dataset
uspto-grants-2014_06
Patent number
US08742132B2

Reaction notes

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