Triethylamine → 6-chloro-3,4-dihydro-3-oxo-N-[1-(3-phenoxypropyl)-4-piperidyl]-2H-1,4-benzoxazine-8-carboxamide hydrochloride

HRID 329729

Reaktionsgleichung

Reaktionsgleichung von HRID 329729
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=O)[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[NH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH2:36][CH2:37][CH2:38][O:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[CH2:32][CH2:31]1>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([NH:29][CH:30]2[CH2:31][CH2:32][N:33]([CH2:36][CH2:37][CH2:38][O:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:34][CH2:35]2)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[NH:7][C:6]=2[CH:12]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 147198366-Chloro-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acidHCID 148021201-(3-Phenoxypropyl)piperidin-4-amine

Produkt 1

HCID 198711536-chloro-3,4-dihydro-3-oxo-N-[1-(3-phenoxypropyl)-4-piperidyl]-2H-1,4-benzoxazine-8-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2.3 g of 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 100 ml of tetrahydrofuran is cooled to below 0° C. and 2 ml of triethylamine is added under stirring thereto. Further, 1.1 g of ethyl chlorocarbonate is added and the mixture is stirred for 3 hours. To the resultant mixture is added 2.5 g of 4-amino-1-(3-phenoxypropyl)piperidine and the mixture stirred for 8 hours followed by collecting by filtration and washing with tetrahydrofuran and water. To a suspension of thus obtained crystals in 100 ml of methanol are added 10 ml of 10% hydrochloric acid and 30 ml of water and then the suspension is stirred. The collection of the crystals by filtration gives 6-chloro-3,4-dihydro-3-oxo-N-[1-(3-phenoxypropyl)-4-piperidyl]-2H-1,4 -benzoxazine-8-carboxamide hydrochloride, melting at 290°-300° C. with decomposition.

Aufarbeitung

  1. stirringthe mixture is stirred for 3 hours
  2. stirringthe mixture stirred for 8 hours
  3. filtrationby collecting by filtration
  4. washwashing with tetrahydrofuran and water
  5. additionTo a suspension of thus obtained crystals in 100 ml of methanol
  6. additionare added 10 ml of 10% hydrochloric acid and 30 ml of water
  7. stirringthe suspension is stirred
  8. customThe collection of the crystals
  9. filtrationby filtration

Quellen und Nachweise

ORD-Eintrag
ord-fb1a7cbae0144f33855a560d2893804c
Quelldatensatz
uspto-grants-1990_01
Patentnummer
US04892872

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