Piperidine → Acemetacin

HRID 542587

反応式

HRID 542587 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 1981Acemetacin

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-86f99fbf4277483ca14ccb71c12ba64b
出典データセット
uspto-grants-1987_04
特許番号
US04658039

関連ノート

読み込み中…