Benzhydrylpiperazine → HCID 66679934, compound

HRID 1626760Notes

Reaction equation

HRID 1626760 reaction equation
C(N(CC)C(C)C)(C)C.Cl[C:11](OC1C=CC([N+]([O-])=O)=CC=1)=[O:12].[NH2:23][C:24]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27].[CH:35]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(OCC)(=O)C.C1COCC1.C(Cl)(Cl)Cl>[Cl:34][C:31]1[CH:32]=[CH:33][C:24]([NH:23][C:11]([N:51]2[CH2:52][CH2:53][N:48]([CH:35]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:49][CH2:50]2)=[O:12])=[C:25]([CH:30]=1)[C:26]([O:28][CH3:29])=[O:27]

Participants

7

Reactant 4

HCID 70048BenzhydrylpiperazineHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 66679934HCID 66679934, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21956068Chloroform tetrahydrofuranSolvent

Procedure

0.77 g (5.9 mmol) of N,N-diisopropylethylamine and 1.19 g (5.9 mmol) of p-nitrophenyl chloroformate were added to a mixed solution of THF/chloroform (30 mL/60 mL) comprising 1.0 g (5.4 mmol) of methyl 2-amino-5-chlorobenzoate at 0° C. The mixture was stirred at room temperature for 1.5 hours. Thereafter, 1.36 g (5.4 mmol) of 1-benzhydrylpiperazine was added at room temperature, and the mixture was stirred for 16 hours. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate and filtered through silica gel. The resulting organic layer was condensed under reduced pressure, and the residue was recrystallized with ethyl acetate/n-hexane, thereby giving 1.81 g of methyl 5-chloro-2-({[4-(diphenylmethyl)piperazine-1-yl]carbonyl}amino)benzoate (yield: 73%).

Workup

  1. customat 0° C
  2. stirringthe mixture was stirred for 16 hours
  3. washthe mixture was washed with saturated saline
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered through silica gel
  6. customcondensed under reduced pressure
  7. customthe residue was recrystallized with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-5b9aed78277e45aaacc555068bf72139
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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