HCID 68464317, compound → 1,2,3,4-Tetrahydro[1]benzofuro[2,3-c]pyridine

HRID 501217Notes

Reaction equation

HRID 501217 reaction equation
[CH2:1]1[C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][N:2]1C(OC)=O>Cl>[CH2:1]1[C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH2:4][CH2:3][NH:2]1

Participants

3

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 3,4-dihydro[1]benzofuro[2,3-c]pyridine-2(1H)-carboxylate (0.150 g, 0.6493 mmol) and concentrated HCl (10 ml) was refluxed for 18 h. The reaction mixture was cooled to 0° C., quenched with saturated aqueous NaHCO3 (100 mL), and extracted with ethyl acetate (2×50 mL), the organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to furnish 1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine (0.1 g, 46%). 1H NMR (200 MHz, CDCl3): δ 3.15 (m, 4H), 4.40 (m, 2H), 7.35 (m, 2H), 7.51 (m, 2H). MS: 160 (M+).

Workup

  1. temperaturewas refluxed for 18 h
  2. customquenched with saturated aqueous NaHCO3 (100 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialthe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fef43a6f14b14b45a8620f020ec18ac1
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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