Hydrochloric Acid → HCID 2729059, compound

HRID 501211Notes

Reaction equation

HRID 501211 reaction equation
II.Br[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH3:11].BrCCBr.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26](=[O:29])[CH2:25][CH2:24]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl.[OH-].[Na+]>C1COCC1>[CH2:24]1[C:11]2[O:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:18]=2[CH2:17][CH2:16][NH:23]1.[CH2:16]([N:23]1[CH2:28][CH2:27][C:26]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:10][CH3:11])([OH:29])[CH2:25][CH2:24]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 807IodineHCID 78391,2-DibromoethaneHCID 113582-BromoanisoleHCID 14798Sodium HydroxideHCID 192201-Benzyl-4-piperidone

Product 2

HCID 2729059HCID 2729059, compoundYield 113.3%HCID 139252351,2,3,4-Tetrahydro[1]benzofuro[2,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1,2,3,4-Tetrahydro[1]benzofuro[2,3-c]pyridine was prepared by the method described by Jaen, J. and Wise, L. D.; J. Heterocycl. Chem. 1987, 1317-1319. To a reaction mixture containing Mg turnings (0.85, 35.41 mmol), a pinch of iodine in THF (5 mL) under N2 atmosphere was added a mixture of 2-bromoanisole (5.0 g, 26.7 mmol) and 1,2-dibromoethane (1.4 g, 8.8 mmol) in (10 mL) THF. When all the magnesium was consumed, a solution of 1-benzyl-4-piperidone (5.0 g, 28.24 mmol) in THF (10 mL) was added dropwise. Following the addition, the solution was refluxed for 20 minutes, and then stirred at room temperature for 2 h. The reaction mixture cooled to 0° C. and 10% HCl was added dropwise until the pH of the mixture was 1-2. The pH was adjusted to 10 with 2N NaOH and extracted with ether (2×100 mL). The organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to furnish 1-benzyl-4-(2-methoxyphenyl)piperidin-4-ol (4.5 g, 90%). 1H NMR (200 MHz, CDCl3): δ 2.20 (d, J=17 Hz, 2H), 2.60-3.15 (m, 2H), 3.20-3.50 (m, 4H), 3.90 (s, 3H), 4.20 (d, J=7 Hz, 2H), 6.90-7.05 (m, 2H), 7.20-7.35 (m, 2H), 7.35-7.55 (m, 3H), 7.60-7.80 (m, 2H); m/e=297.

Workup

  1. customWhen all the magnesium was consumed
  2. additionthe addition
  3. temperaturethe solution was refluxed for 20 minutes
  4. temperatureThe reaction mixture cooled to 0° C.
  5. extractionextracted with ether (2×100 mL)
  6. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f43bfd34b4e4614a261ca7e96d328f3
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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