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Diisopropylethylamine → 3-benzhydryl-1-(2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl)benzyl]piperazine dihydrochloride

HRID 1006356
Notes
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Reaction equation

HRID 1006356 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:15].Cl.[CH:17]([CH:30]1[CH2:35][NH:34][CH2:33][CH2:32][NH:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C.[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:52]([N:55]2[C:59]([C:60]([F:63])([F:62])[F:61])=[N:58][N:57]=[N:56]2)=[CH:51][C:48]=1[CH:49]=O>ClCCl.C(O)(=O)C>[ClH:15].[ClH:15].[CH:17]([CH:30]1[NH:31][CH2:32][CH2:33][N:34]([CH2:49][C:48]2[CH:51]=[C:52]([N:55]3[C:59]([C:60]([F:63])([F:62])[F:61])=[N:58][N:57]=[N:56]3)[CH:53]=[CH:54][C:47]=2[O:46][CH3:45])[CH2:35]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113916182-Methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehydeHCID 226747432-Benzhydrylpiperazine dihydrochloride

Product 1

HCID 226745813-benzhydryl-1-(2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl)benzyl]piperazine dihydrochloride
Yield 84.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (127 mg) was added portionwise to a mixture of 2-benzhydrylpiperazine dihydrochloride (97.6 mg), N,N-diisopropylethylamine (0.104 ml) and 2-methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehyde (61.2 mg) in a mixture of dichloromethane (5 ml) and acetic acid (1 drop) 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 (70:1). The fractions containing the objective compound were collected, evaporated under reduced pressure and treated with 4N hydrogen chloride in ethyl acetate solution to give 3-benzhydryl-1-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]piperazine dihydrochloride (74 mg) as a colorless powder.

Workup

  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 (70:1)
  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

Sources & evidence

ORD record
ord-c1a94ecd69b641308f0f38912a2145a5
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06787543B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes