Hydrochloric Acid → 3-Phenyl-3H-spiro[2-benzofuran-1,4'-piperidine]

HRID 1077322Notes

Reaction equation

HRID 1077322 reaction equation
C1([N:7]2[CH2:12][CH2:11][C:10]3([C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][O:13]3)[CH2:9][CH2:8]2)C=CC=CC=1.Cl>[Pd].C(O)C>[C:15]1([CH:14]2[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10]3([CH2:9][CH2:8][NH:7][CH2:12][CH2:11]3)[O:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86733482HCID 86733482, compound

Product 1

HCID 1915103-Phenyl-3H-spiro[2-benzofuran-1,4'-piperidine]

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2.9 G. of 1'-benzyl-1,3-dihydro-3-phenylspiro[phenylspiro[isobenzofuran-1,4'-piperidine], (Example 4), 0.4 g. of 10% palladium on carbon, 20 ml. of 95% ethanol, and 2 ml. of conc. hydrochloric acid is hydrogenated at 50 p.s.i. and 50°. After hydrogen uptake ceases, the mixture is filtered and the filtrate concentrated. Recrystallization of the residue from cyclohexane provides colorless crystals, m.p. 119°-123°.

Workup

  1. additionA mixture of 2.9 G
  2. custom50°
  3. filtrationAfter hydrogen uptake ceases, the mixture is filtered
  4. concentrationthe filtrate concentrated
  5. customRecrystallization of the residue from cyclohexane
  6. customprovides colorless crystals, m.p. 119°-123°

Sources & evidence

ORD record
ord-9c2f915bdfe7497d8e74b2e39d611e7b
Source dataset
uspto-grants-1976_05
Patent number
US03959475

Reaction notes

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