Acetic Acid → 4H-Spiro[chromene-3,4'-piperidine]

HRID 270045Notes

Reaction equation

HRID 270045 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][CH2:14]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>CO.[Pd]>[NH:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[O:15][CH2:14]2)[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59833652HCID 59833652, compound

Product 1

HCID 151870484H-Spiro[chromene-3,4'-piperidine]Yield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1′-benzyl-4H-spiro[chromene-3,4′-piperidine] (800 mg, 2.7 mmol) was dissolved in methanol (100 mL). Acetic acid (5 mL) and palladium on activated charcoal (cat amount, 10%) was added. Reaction in a Parr apparatus at 35 psi for 18 hrs, followed by filtration, evaporation and HPLC purification on C18 (acetonitrile/water) yielded 500 mg (92%) of the title compound.

Workup

  1. customReaction in a Parr apparatus at 35 psi for 18 hrs
  2. filtrationfollowed by filtration, evaporation and HPLC purification on C18 (acetonitrile/water)

Sources & evidence

ORD record
ord-82189480b1114b4e85421f1c01a770f9
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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