2-(2,4-Dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole → 4-(3-Morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole

HRID 41418Notes

Reaction equation

HRID 41418 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][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH2:7]1>FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.C(OCC)C.CO>[N:19]1([CH2:18][CH2:17][CH2:16][O:15][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]3[C:13]=2[CH2:14][NH:6][CH2:7]3)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

6

Reactant 1

HCID 592631052-(2,4-Dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole

Product 1

HCID 469151864-(3-Morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindoleYield 236.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

A solution of 2-(2,4-dimethoxy-benzyl)-4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole (233 mg, 0.56 mmol) in trifluoroacetic acid (1.0 mL) and anisole (0.5 mL) was heated at 150° C. under microwave irradiation for 10 minutes. The mixture was diluted with diethyl ether and extracted twice with water. The combined aqueous extracts were concentrated to give an oil which was dissolved in methanol and concentrated in vacuo to afford the title compound as a brown oil (348 mg, including residual TFA and/or water). 1H NMR (methanol-d4) 7.40 (1H, t), 7.03 (1H, d), 6.99 (1H, d), 4.63 (2H, s), 4.59 (2H, s), 4.21 (2H, t), 4.14-4.04 (2H, m), 3.85-3.73 (2H, m), 3.61-3.52 (2H, m), 3.41-3.36 (2H, m), 3.25-3.13 (2H, m), 2.32-2.25 (2H, m). MS: [M+H]+ 263.

Workup

  1. extractionextracted twice with water
  2. concentrationThe combined aqueous extracts were concentrated
  3. customto give an oil which
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d949ecbfbf91462aa617e443fc057899
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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