Hydrochloric Acid → 2-[2-(4-Hydroxy-4-phenylpiperidino)ethyl]-1,4-benzodioxan hydrochloride

HRID 1391064

Reaktionsgleichung

Reaktionsgleichung von HRID 1391064
O1C2C=CC=CC=2OCC1CC=O.OC1(C2C=CC=CC=2)CCNCC1.[ClH:27].[OH:28][C:29]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:34][CH2:33][N:32]([CH:35]=[CH:36][CH:37]2[O:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[O:39][CH2:38]2)[CH2:31][CH2:30]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CO>[ClH:27].[OH:28][C:29]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[CH2:30][CH2:31][N:32]([CH2:35][CH2:36][CH:37]2[O:42][C:41]3[CH:43]=[CH:44][CH:45]=[CH:46][C:40]=3[O:39][CH2:38]2)[CH2:33][CH2:34]1

Komponenten

8

Edukt 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 963874-Phenylpiperidin-4-olHCID 5003444Sodium cyanoborohydrideHCID 21331989(2,3-Dihydro-1,4-benzodioxin-2-yl)acetaldehydeHCID 539274311-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethenyl]-4-phenylpiperidin-4-ol

Produkt 1

HCID 213320052-[2-(4-Hydroxy-4-phenylpiperidino)ethyl]-1,4-benzodioxan hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To the solution of 10 g of 1,4-benzodioxan-2-yl-acetaldehyde and 12.7 g of 4-hydroxy-4-phenylpiperidine in 300 ml of methanol is added 8 ml of 4.5 N ethanolic hydrogen chloride at which conditions the 2-[2-(4-hydroxy-4-phenylpiperidino)-vinyl]-1,4-benzodioxan is formed in situ. After standing for one hour, at room temperature the solution of 2.4 g of sodium cyanoborohydride in 30 ml of methanol is added dropwise while stirring. After one hour the solution is made strongly basic with aqueous sodium hydroxide, concentrated to a small volume and diluted with water. The mixture is extracted with ethyl acetate, the extract dried and evaporated. The residue is treated with ethanolic hydrogen chloride and the precipitate recrystallized from ethanoldiethyl ether, to yield the 2-[2-(4-hydroxy-4-phenylpiperidino)-ethyl]-1,4-benzodioxan hydrochloride melting at 203°.

Aufarbeitung

  1. customis formed in situ
  2. concentrationconcentrated to a small volume
  3. additiondiluted with water
  4. extractionThe mixture is extracted with ethyl acetate
  5. customthe extract dried
  6. customevaporated
  7. additionThe residue is treated with ethanolic hydrogen chloride
  8. customthe precipitate recrystallized from ethanoldiethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-2672c28202c84eb29e0aa72b7dea2c1f
Quelldatensatz
uspto-grants-1979_02
Patentnummer
US04140781

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