Formaldehyde → 2-benzhydryl-4-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-1-methylpiperazine dihydrochloride

HRID 1006357Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006357
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.[ClH:17].Cl.[CH:19]([CH:32]1[NH:37][CH2:36][CH2:35][N:34]([CH2:38][C:39]2[CH:44]=[C:43]([N:45]3[C:49]([C:50]([F:53])([F:52])[F:51])=[N:48][N:47]=[N:46]3)[CH:42]=[CH:41][C:40]=2[O:54][CH3:55])[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl.CO>[ClH:17].[ClH:17].[CH:19]([CH:32]1[CH2:33][N:34]([CH2:38][C:39]2[CH:44]=[C:43]([N:45]3[C:49]([C:50]([F:53])([F:52])[F:51])=[N:48][N:47]=[N:46]3)[CH:42]=[CH:41][C:40]=2[O:54][CH3:55])[CH2:35][CH2:36][N:37]1[CH3:1])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Komponenten

6

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 226745813-benzhydryl-1-(2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl)benzyl]piperazine dihydrochloride

Produkt 1

HCID 226745552-benzhydryl-4-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-1-methylpiperazine dihydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Sodium triacetoxyborohydride (146 mg) was added portionwise to a mixture of 37% aqueous formaldehyde (30 mg) and 3-benzhydryl-1-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]piperazine dihydrochloride in a mixture of dichloromethane (4 ml) and methanol (2 drops) at 0° C. and the whole was stirred at 5° C.˜room temperature overnight. The mixture was partitioned between ethyl acetate and 2N sodium hydroxide. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (60:1). The fractions containing the objective compound were collected and evaporated under reduced pressure and treated with 4N hydrogen chloride in ethyl acetate solution to give 2-benzhydryl-4-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-1-methylpiperazine dihydrochloride (32.9 mg) as a colorless powder.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and 2N sodium hydroxide
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by column chromatography on silica gel using a mixed solvent of dichloromethane and methanol (60:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure
  10. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Quellen und Nachweise

ORD-Eintrag
ord-5a6e03f5f87f444d80546aafcd2e71cb
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787543B2

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