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Bromodiphenylmethane → 2-[4-[3-(Diphenylmethoxy)propyl]-1-piperazinyl]pyrimidine

HRID 35369
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 35369
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[N:7]1[CH2:12][CH2:11][N:10]([CH:13](O)[CH2:14][CH3:15])[CH2:9][CH2:8]1.[C:17]1([CH:23](Br)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-:32].[Na+]>CN(C)C=O>[C:17]1([CH:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:32][CH2:15][CH2:14][CH2:13][N:10]2[CH2:11][CH2:12][N:7]([C:2]3[N:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH2:8][CH2:9]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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Komponenten

5

Edukt 3

HCID 236603BromodiphenylmethaneHCID 516892Sodium BicarbonateHCID 212792541-(2-Pyrimidinyl)-4-piperazinyl propanol

Produkt 1

HCID 142339542-[4-[3-(Diphenylmethoxy)propyl]-1-piperazinyl]pyrimidineAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-(2-pyrimidinyl)-4-piperazinyl propanol 3 g. (0.013 mol) in 50 mol. of dimethylformamide was added 3.3 g. (0.013 mol) of diphenylmethylbromide and 2.9 g. (0.034 mol) of sodium bicarbonate. The reaction mixture was refluxed overnight, dimethylformamide was evaporated under reduced pressure, and the residue was extracted with methylene chloride (400 ml.). The methylene chloride extracts were collected, washed with water and evaporated, and the remaining residue was purified by HPLC to give 1.3 g. (26% yield) of the title compound. The free base which was converted to the (1:1) fumarate salt; m.p 166°-168° C.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. customdimethylformamide was evaporated under reduced pressure
  3. extractionthe residue was extracted with methylene chloride (400 ml.)
  4. customThe methylene chloride extracts were collected
  5. washwashed with water
  6. customevaporated
  7. customthe remaining residue was purified by HPLC
  8. customto give 1.3 g

Quellen und Nachweise

ORD-Eintrag
ord-db1c7b5655734fdd82605a2897516b93
Quelldatensatz
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04766215

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