1-Phenylpiperazine → 1-[[(4-Phenyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448732Notes

Reaction equation

HRID 448732 reaction equation
[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH2:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:18](OC(OC(C)(C)C)=O)(OC(C)(C)C)=[O:19].C(N(CC)CC)C.[C:40]1([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:1]1([CH2:7][O:8][C:9]([C:11]2([NH:17][C:18]([N:49]3[CH2:50][CH2:51][N:46]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH2:47][CH2:48]3)=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 15176238Benzyl 1-aminocyclohexanecarboxylate

Product 1

HCID 576728411-[[(4-Phenyl-1-piperazinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl esterYield 70.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 366 mg (3 mmol) of N,N-dimethylaminopyridine and 6.99 g (30 mmol) of 1-aminocyclohexanecarboxylic acid phenylmethyl ester in methylene chloride was added to a solution of 6.55 g (30 mmol) of di-t-butyl dicarbonate in 150 ml of methylene chloride, and the mixture was stirred at room temperature for 30 minutes. Thereafter, a solution of 6.07 g (60 mmol) of triethylamine and 5.11 g (33 mmol) of 1-phenylpiperazine in methylene chloride was added, and the mixture was stirred at room temperature overnight. The reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the obtained crystal was washed with diethyl ether to obtain 8.88 g (70%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction solution was concentrated
  3. additionethyl acetate was added
  4. washthe mixture was successively washed with water
  5. dry with materialby drying with anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off under reduced pressure
  7. washthe obtained crystal was washed with diethyl ether

Sources & evidence

ORD record
ord-a18c4306a07f40c9b5921a72f2bcc5ba
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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