Formaldehyde → 7-Iodo-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine

HRID 1616910Notes

Reaction equation

HRID 1616910 reaction equation
[CH2:1]=O.Cl.[I:4][C:5]1[CH:16]=[CH:15][C:8]2[C:9]([CH2:12][CH2:13][NH2:14])=[CH:10][O:11][C:7]=2[CH:6]=1>Cl.C=O>[I:4][C:5]1[CH:16]=[CH:15][C:8]2[C:9]3[CH2:12][CH2:13][NH:14][CH2:1][C:10]=3[O:11][C:7]=2[CH:6]=1

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 673240032-(6-Iodobenzofuran-3-yl)ethanamine hydrochloride

Product 1

HCID 673248767-Iodo-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridineYield 103.8%

Reagents, catalysts & solvents 2

HCID 712FormaldehydeCatalystHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
70 °C

Procedure

Paraformaldehyde (8.9 g, 0.297 mol) was added to a solution of 2-(6-iodo-1-benzofuran-3-yl)ethanamine hydrochloride (80 g; 0.247 mol) in 1N HCl (500 mL) under N2. After 2 h stirring at 70° C., another portion of paraformaldehyde (740 mg) was added. The reaction mixture was cooled down to r.t., filtered, the resulting solid was washed with 1N HCl (100 mL), dried overnight under house vacuum to afford 76.7 g of the title product as a hydrochloric acid salt. 1H-NMR (400 MHz, CDCl3): δ 2.06 (bt, 2H), 2.92 (bt, 2H), 4.37 (s, 2H), 7.45 (d, 1H) 7.62 (dd, 1H), 8.05 (d, 1H), 10.04 (bs, 2H).

Workup

  1. temperatureThe reaction mixture was cooled down to r.t.
  2. filtrationfiltered
  3. washthe resulting solid was washed with 1N HCl (100 mL)
  4. customdried overnight under house vacuum

Sources & evidence

ORD record
ord-aa96e2549f954b9093dec4d12cfdf7d5
Source dataset
uspto-grants-2014_07
Patent number
US08765779B2

Reaction notes

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