Ethyl acetate hexane → 4-{4-[4-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carbonyl]-piperazin-1-yl}-1-phenyl-cyclohexanecarbonitrile

HRID 1167721Notes

Reaction equation

HRID 1167721 reaction equation
[N+](C1C=CC(O[C:11]([N:13]2[CH:17]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=3)[CH2:16][O:15][C:14]2=[O:26])=[O:12])=CC=1)([O-])=O.[C:27]1([C:33]2([C:45]#[N:46])[CH2:38][CH2:37][CH:36]([N:39]3[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]3)[CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CCCCCC.CCOC(C)=O>C1COCC1>[F:25][C:20]1[CH:19]=[C:18]([CH:17]2[CH2:16][O:15][C:14](=[O:26])[N:13]2[C:11]([N:42]2[CH2:41][CH2:40][N:39]([CH:36]3[CH2:37][CH2:38][C:33]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)([C:45]#[N:46])[CH2:34][CH2:35]3)[CH2:44][CH2:43]2)=[O:12])[CH:23]=[CH:22][C:21]=1[F:24]

Participants

5

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 220490874-(3,4-Difluorophenyl)-3-(4-nitrophenyloxy-carbonyl)-2-oxo-oxazolidineHCID 229934561-Phenyl-4-piperazin-1-yl-cyclohexanecarbonitrile

Product 1

HCID 104358404-{4-[4-(3,4-Difluoro-phenyl)-2-oxo-oxazolidine-3-carbonyl]-piperazin-1-yl}-1-phenyl-cyclohexanecarbonitrileYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-(3,4-difluoro-phenyl)-2-oxo-oxazolidine-3-carboxylic acid 4-nitrophenyl ester (80 mg, 0.21 mmol) in 5 ml of THF was added 1-phenyl-4-piperazin-1-yl-cyclohexanecarbonitrile (80 mg, 0.29 mmol) in a portion and the resulting solution was stirred for 12 h at 25° C. Reaction mixture was concentrated in vacuo yielding a yellow oil, which was subjected to column chromatography (50% Hexane/EtOAc) to provide 53 mg (51%) of the desired product as a colorless oil. The product obtained was converted to the HCl salt and recrystallized from EtOAc-Et2O to afford 43 mg of the product as white solid: mp 148-151° C.; Anal. Calc. For C27H28F2N4O3.1.0HCl requires C, 61.07; H, 5.50; N, 10.55. Found: C, 59.48; H, 5.41; N, 10.34.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo
  3. customyielding a yellow oil, which

Sources & evidence

ORD record
ord-64d8fac8d19341caa6ec5b3473793a9b
Source dataset
uspto-grants-2003_09
Patent number
US06620815B1

Reaction notes

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