Hydrogen chloride-ethyl acetate → phenylmethyl 1-[N-(piperazine-1-carbonyl)amino]cyclohexanecarboxylate

HRID 1953432Notes

Reaction equation

HRID 1953432 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([NH:16][C:17]2([C:23]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[CH2:10][CH2:9]1)=O)(C)C.Cl.C(OCC)(=O)C>C(OCC)(=O)C.Cl>[N:11]1([C:14]([NH:16][C:17]2([C:23]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 53984920phenylmethyl 1-[N-[4-(2-methyl-2-propyloxycarbonyl)piperazine-1-carbonyl]amino]cyclohexanecarboxylate

Product 1

HCID 23297891phenylmethyl 1-[N-(piperazine-1-carbonyl)amino]cyclohexanecarboxylateYield 87.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.5 g (5.6 mmol) of phenylmethyl 1-[N-[4-(2-methyl-2-propyloxycarbonyl) piperazine-1-carbonyl]amino]cyclohexanecarboxylate synthesized in Reference Example 8 was dissolved in ethyl acetate and 14 ml (56 mmol) of 4N hydrogenchloride-ethyl acetate solution (56 mmol) was added to the above prepared mixture under 0° C. and stirred for 3 hours at the room temperature. After completion of concentration of the reaction solution, the reaction solution was dissolved in 1N hydrochloric acid and washed with ethyl acetate. The water layer was separated out and was made into pH 9 with the addition of sodium carbonate and extracted three times with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, whereby 1.7 g of phenylmethyl 1-[N-(piperazine-1-carbonyl)amino]cyclohexanecarboxylate was obtained.

Workup

  1. washwashed with ethyl acetate
  2. customThe water layer was separated out
  3. additionwas made into pH 9 with the addition of sodium carbonate
  4. extractionextracted three times with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2ecc96b7780e4d0998e17af5ce964204
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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