1'-Benzylspiro[isochroman-1,4'-piperidine] → 3,4-Dihydrospiro[2-benzopyran-1,4'-piperidine]

HRID 1182729Notes

Reaction equation

HRID 1182729 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][O:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][C:11]2([C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][CH2:15][O:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 102664131'-Benzylspiro[isochroman-1,4'-piperidine]HCID 178418361HCID 178418361, compound

Product 1

HCID 151870503,4-Dihydrospiro[2-benzopyran-1,4'-piperidine]Yield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1′-benzyl-3,4-dihydrospiro[isochromene-1,4′-piperidine] (0.40 g, 1.3 mmol) in ethanol (15 ml) was purged with argon. After addition of the palladium catalyst (10% Pd on activated charcoal, 0.14 g) the reaction vessel was filled with hydrogen gas. The mixture was stirred for 18 h at room temperature. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to give the title compound (0.23 g) as white solid with a purity of approx. 88% as assessed by 1H-NMR (contaminated with 1′-ethyl-3,4-dihydrospiro[isochromene-1,4′-piperidine]). MS m/e: 204 (M+H+).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fedfb15c53e844d29a4fcac24e00b933
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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