Piperidine → Acemetacin

HRID 542587

Reaction equation

HRID 542587 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH3:18])=[CH:14][CH:15]=3)[C:10]([CH2:19][C:20]([O:22][CH2:23][C:24]([O:26]CC=C)=[O:25])=[O:21])=[C:9]2[CH3:30])=[O:7])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1CCCCC1>[Pd].C1(C)C=CC=CC=1>[CH3:30][C:9]1[N:8]([C:6]([C:5]2[CH:31]=[CH:32][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:7])[C:16]2[CH:15]=[CH:14][C:13]([O:17][CH3:18])=[CH:12][C:11]=2[C:10]=1[CH2:19][C:20]([O:22][CH2:23][C:24]([OH:26])=[O:25])=[O:21]

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11776TriphenylphosphineHCID 13654465Allyl 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-3-indoleacetoxyacetate

Product 1

HCID 1981Acemetacin

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Procedure

31.9 g of acemetacin allyl ester, 100 ml of toluene, 2.3 g of triphenylphosphine and 0.75 g of palladium on charcoal (5% strength) are taken as an initial charge, under nitrogen. 11.9 g of piperidine are added dropwise, with stirring, and the mixture is then stirred for a further 3 hours at 90° C. It is filtered hot and the catalyst is rinsed with hot toluene. The filtrate is evaporated, the residue is taken up in methylene chloride (about 300 ml) and this solution is washed with half-concentrated hydrochloric acid (100 ml) and then with water. After removal of the solvent in vacuo, the residue is recrystallized from toluene.

Workup

  1. additionan initial charge, under nitrogen
  2. stirringthe mixture is then stirred for a further 3 hours at 90° C
  3. filtrationIt is filtered hot
  4. washthe catalyst is rinsed with hot toluene
  5. customThe filtrate is evaporated
  6. washthis solution is washed with half-concentrated hydrochloric acid (100 ml)
  7. customAfter removal of the solvent in vacuo
  8. customthe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-86f99fbf4277483ca14ccb71c12ba64b
Source dataset
uspto-grants-1987_04
Patent number
US04658039

Linked notes

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