Diethyl Ether → 3H-Spiro(1-benzofuran-2,4'-piperidine)

HRID 261494Notes

Reaction equation

HRID 261494 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.Cl.C(N1CCC2(CC3C=CC=CC=3O2)CC1)C1C=CC=CC=1.[H][H].CCOCC>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

7

Reactant 4

HCID 3283Diethyl EtherHCID 127332271'-(Phenylmethyl)spiro[benzofuran-2(3H),4'-piperidine]HCID 204778142,3-Dihydro-1'-benzylspiro[benzofuran-2,4'-piperidine]hydrochlorideHCID 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 Example 1, in 250 ml of isopropyl alcohol is hydrogenated in a Paar shaker, 50 psig, 65°-70° C., with 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 is 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 is filtered through celite
  5. concentrationconcentrated again
  6. customproviding a white solid which

Sources & evidence

ORD record
ord-4165a27a1aa44a5cb729353c62af55a4
Source dataset
uspto-grants-1979_08
Patent number
US04166119

Reaction notes

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