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Sodium Hydroxide → 1-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-phenoxypiperidine dihydrochloride

HRID 463311
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 463311
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([O:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:29][CH2:28]3)=O)[CH3:23])[O:18][CH2:17][CH2:16][O:15]2)=[CH:10][CH:9]=1.[OH-].[Na+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:54].Cl>C1COCC1.O>[ClH:54].[ClH:54].[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2([CH2:19][CH2:20][CH2:21][N:22]([CH2:24][CH2:25][N:27]3[CH2:28][CH2:29][CH:30]([O:33][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[CH2:31][CH2:32]3)[CH3:23])[O:15][CH2:16][CH2:17][O:18]2)=[CH:12][CH:13]=1
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Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 202831171-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]-propyl}-N-methylaminoacetyl}-4-phenoxypiperidineHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 202830621-{2-{N-{3-[2-(4-Fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylamino}ethyl}-4-phenoxypiperidine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 1.9 g (25.1 mmol) of lithium aluminum hydride (50% in oil; washed three times with hexane) in 75 ml dry THF, cooled by an ice bath, was added dropwise a solution of 1-{N-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-N-methylaminoacetyl}-4-phenoxypiperidine (from above) in 75 ml of dry THF. The suspension was heated at reflux for 12 hours and allowed to cool to room temperature. To the mixture, in an ice bath were added slowly dropwise 1 ml of water, 1 ml of 15% NaOH and 3 ml of water. The mixture was filtered and washed with THF. The solvent was evaporated from the filtrate to provide an oil which was extracted with ether and washed with saturated sodium chloride. The solution was dried over potassium carbonate and filtered to provide an oil. The overall yield of the dihydrochloride was 7.47 g (82.0%).

Aufarbeitung

  1. temperaturecooled by an ice bath
  2. temperatureThe suspension was heated
  3. temperatureat reflux for 12 hours
  4. filtrationThe mixture was filtered
  5. washwashed with THF
  6. customThe solvent was evaporated from the filtrate
  7. customto provide an oil which
  8. extractionwas extracted with ether
  9. washwashed with saturated sodium chloride
  10. dry with materialThe solution was dried over potassium carbonate
  11. filtrationfiltered
  12. customto provide an oil

Quellen und Nachweise

ORD-Eintrag
ord-bea82bf36232476a840a072b76318466
Quelldatensatz
uspto-grants-1985_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04518713

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