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

HRID 1454318Notes

Reaction equation

HRID 1454318 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 drop wise a solution of TFA (1 mL) in methylene chloride (5mL). 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-5966e487e5754f6cae8f3f210780f8e1
Source dataset
uspto-grants-2009_01
Patent number
US07479500B2

Reaction notes

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