Trifluoroacetic acid → 1,2,3,6-Tetrahydro-4-(7-methoxy-3-benzofuranyl)pyridine

HRID 495416Notes

Reaction equation

HRID 495416 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=3[O:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:24][O:23][C:22]1[C:17]2[O:16][CH:15]=[C:14]([C:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20827141HCID 20827141, compound

Product 1

HCID 223269391,2,3,6-Tetrahydro-4-(7-methoxy-3-benzofuranyl)pyridineYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 4-(7-methoxy-benzofuran-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.50 g, 1.5 mmol) in methylene chloride (10 mL), was added dropwise a solution of TFA (1 mL) in methylene chloride (5 mL). The reaction was stirred at room temperature for one hour, then was diluted with 250 mL of methylene chloride, washed with 1N NaOH (100 mL) and with saturated brine, dried over magnesium sulfate, filtered and concentrated in vacuum to give 0.30 g of the title compound. 1H NMR (300 MHz, CDCl3); δ 2.5 (t, 2H), 3.19 (t, 2H), 3.64 (dd, 2H), 4.01 (s, 3H), 6.30 (br s, 1H), 7.10 (d, 1H), 7.21 (t, 1H), 7.52 (d, 1H), 7.64 (s, 1H); MS (ES) m/z (relative intensity): 230 (M+H, 100).

Workup

  1. washwashed with 1N NaOH (100 mL) and with saturated brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-0c2daa6cd36a4b0481cb7be15b74e6b9
Source dataset
uspto-grants-2005_09
Patent number
US06939877B2

Reaction notes

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