Formaldehyde → HCID 21481152, Verbindung

HRID 435646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 435646
N[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.C=O.[C:33](#N)C.[C:36]([BH3-])#[N:37].[Na+]>C(O)(=O)C>[CH3:33][N:37]([CH3:36])[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 21481150HCID 21481150, Verbindung

Produkt 1

HCID 21481152HCID 21481152, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel2×

Versuchsvorschrift

7 g of 3-[2-[4-(2-amino-10,11-dihydro-dibenzo[b,f]-thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone, 13.1 ml of 40% formaldehyde and 61 ml of acetonitrile are treated with 3.32 of sodium cyanoborohydride and the resulting mixture is treated dropwise over period of 10 minutes with 1.5 ml of acetic acid. The mixture is stirred for a further 90 minutes, treated dropwise with a further 1.5 ml of acetic acid and again stirred for 15 minutes. The mixture is now extracted with 200 ml of ether and the organic phase washed three times with 1-N aqueous potassium hydroxide solution, dried over sodium sulphate and evaporated. There is obtained 3-[2-[4-(10,11-dihydro-2-dimethylamino-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl]-2-oxazolidinone which melts at 168°-170° C. After recrystallisation from ethanol, this compound melts at 171°-173° C. By treatment with maleic acid there is obtained the corresponding maleate which melts at 143.5°-144.5° C after recrystallisation from acetonitrile.

Aufarbeitung

  1. stirringagain stirred for 15 minutes
  2. extractionThe mixture is now extracted with 200 ml of ether
  3. washthe organic phase washed three times with 1-N aqueous potassium hydroxide solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3b5e72521f244ed2b6f59067f3049aa2
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04006145

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