1'-(Phenylmethyl)spiro[benzofuran-2(3H),4'-piperidine] → 3H-Spiro(1-benzofuran-2,4'-piperidine)

HRID 261469Notes

Reaction equation

HRID 261469 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)(C)C.[Pd]>[NH:8]1[CH2:13][CH2:12][C:11]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 127332271'-(Phenylmethyl)spiro[benzofuran-2(3H),4'-piperidine]HCID 178418361HCID 178418361, compound

Product 1

HCID 127332303H-Spiro(1-benzofuran-2,4'-piperidine)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

A solution of 5.3 g of 2,3-dihydro-1'-benzylspiro[benzofuran-2,4'-piperidine], free base of B, in 250 ml of isopropyl alcohol is hydrogenated with a Paar shaker, 50 psig, 65°-70° C. and 1 g of a 10% palladium/carbon catalyst until the uptake of hydrogen is completed. Thereafter, the solution is successively permitted to cool to ambient temperature, filtered and concentrated to dryness, leaving a white solid. The solid is dissolved in a benzene-ether mixture, the solution filtered through celite and then concentrated again providing a white solid, which upon trituration with ether, provides the product, 2,3-dihydrospiro[benzofuran-2,4'-piperidine], mp 56°-58.5° C.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to dryness
  3. customleaving a white solid
  4. filtrationthe solution filtered through celite
  5. concentrationconcentrated again
  6. customproviding a white solid, which upon trituration with ether

Sources & evidence

ORD record
ord-99c662b7e86b41ef9d75ebd3247127d6
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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