Ethanol → 1-{7-[(3-Fluorophenyl)sulfonyl]-1-methyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridin-1-yl}methanamine

HRID 1616885Notes

Reaction equation

HRID 1616885 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]3[C:17]4[CH2:22][CH2:21][NH:20][C:19]([CH2:24][N:25]5C(=O)C6C(=CC=CC=6)C5=O)([CH3:23])[C:18]=4[O:36][C:13]=3[CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.C(O)C.O.NN>>[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:16]=[CH:15][C:14]3[C:17]4[CH2:22][CH2:21][NH:20][C:19]([CH2:24][NH2:25])([CH3:23])[C:18]=4[O:36][C:13]=3[CH:12]=2)(=[O:9])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 673246722-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione

Product 1

HCID 533269861-{7-[(3-Fluorophenyl)sulfonyl]-1-methyl-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridin-1-yl}methanamine

Procedure

To a solution of 2-[7-(3-fluoro-phenylsulfanyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione (0.150 g, 0.317 mmol) in methanol (10.0 mL, 247 mmol) was added a solution of Oxone® (0.488 g, 0.794 mmol) in water (5.0 mL, 280 mmol) and the reaction mixture was stirred at room temperature overnight. After 3 h, the reaction was filtered, concentrated, and extracted with DCM/sat. aq. NaHCO3. The organic layer was dried, concentrated and purified by chromatography to afford 2-[7-(3-fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione as an off-white solid. A suspension of 2-[7-(3-fluoro-benzenesulfonyl)-1-methyl-1,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl]isoindole-1,3-dione (0.015 g, 0.030 mmol) in ethanol (5.00 mL, 85.6 mmol) was refluxed with hydrazine monohydrate (0.040 mL, 0.80 mmol). After 4 h, the reaction was cooled, filtered, rinsed with MeOH, and the filtrate concentrated and dried under vacuum to afford a yellowish white solid. mp>250° C. dec.; MS m/z 375 [M+H]+. 1H-NMR (400 MHz, CDCl3): δ 1.5 (s, 3H), 2.7 (m, 2H), 3.15 (m, 1H), 3.36 (m, 1H), 4.0 (d, J=14 Hz, 1H), 4.15 (d, J=14 Hz, 1H), 7.2-8.0 (m, 7H)

Workup

  1. temperaturethe reaction was cooled
  2. filtrationfiltered
  3. washrinsed with MeOH
  4. concentrationthe filtrate concentrated
  5. customdried under vacuum
  6. customto afford a yellowish white solid

Sources & evidence

ORD record
ord-e2d057c94a5b474d8b8dafb38e528895
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

Loading…