2-(2,4-Dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole → [2-(2,3-Dihydro-1H-isoindol-4-yloxy)-ethyl]-dimethyl-amine

HRID 334916Notes

Reaction equation

HRID 334916 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH2:7]1>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C(OCC)(=O)C>[CH2:7]1[C:8]2[C:13](=[C:12]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH:11]=[CH:10][CH:9]=2)[CH2:14][NH:6]1

Participants

5

Reactant 1

HCID 592631072-(2,4-Dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole

Product 1

HCID 46915187[2-(2,3-Dihydro-1H-isoindol-4-yloxy)-ethyl]-dimethyl-amineYield 242.4%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2,4-dimethoxy-benzyl)-4-(2-dimethylamino-ethoxy)-2,3-dihydro-1H-isoindole (170 mg, 0.48 mmol) in trifluoroacetic acid (0.5 mL) and anisole (0.5 mL) was heated at 150° C. under microwave irradiation for 10 minutes. The mixture was diluted with ethyl acetate and extracted twice with water. The combined aqueous extracts were concentrated to give the title compound as a purple oil (240 mg, including residual TFA and/or water). 1H NMR (methanol-d4) 7.42 (1H, t), 7.07 (1H, d), 7.04 (1H, d), 4.64 (4H, br.s), 4.47-4.44 (2H, m), 3.65-3.63 (2H, m), 3.01 (6H, s). MS: [M+H]+ 207.

Workup

  1. extractionextracted twice with water
  2. concentrationThe combined aqueous extracts were concentrated

Sources & evidence

ORD record
ord-829ca34a99e24eaab08c85bbaa2c9777
Source dataset
uspto-grants-2014_11
Patent number
US08883790B2

Reaction notes

Loading…