Ethyl Acetate → HCID 46916813, compound

HRID 2189989Notes

Reaction equation

HRID 2189989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:14]1([C@@H:20]([NH:23][C:24]([C:26]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])[CH2:21][CH3:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCCCCCC.[C:45](OCC)(=[O:47])C>C1COCC1>[C:14]1([C@@H:20]([NH:23][C:24]([C:26]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:31][CH2:30][N:29]([C:45]([N:11]3[CH2:12][CH2:13][N:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)[CH2:9][CH2:10]3)=[O:47])[CH2:28][CH2:27]2)=[O:25])[CH2:21][CH3:22])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 8900HeptaneHCID 752601-(4-Fluorophenyl)piperazineHCID 595278574-Phenyl-piperidine-4-carboxylic acid ((S)-1-phenyl-propyl)-amide

Product 1

HCID 46916813HCID 46916813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 66.4 mg (0.409 mmol) N,N′-carbonyldiimidazole in dry THF (4 mL) was added 74 mg (0.409 mmol) 1-(4-fluorophenyl)piperazine and the reaction mixture was stirred at room temperature for 3 h. 40 mg (0.124 mmol) 4-Phenyl-piperidine-4-carboxylic acid ((S)-1-phenyl-propyl)-amide dissolved THF (2 mL) was added. The mixture was heated under reflux for 12 h. The reaction mixture was subjected to flash chromatography with n-heptane and ethyl acetate over a 20 g silica gel column to yield 62 mg 1-[4-(4-fluoro-phenyl)-piperazine-1-carbonyl]-4-phenyl-piperidine-4-carboxylic acid ((S)-1-phenyl-propyl)-amide. MS ISP (m/e): 529.3 (100) [(M+H)+].

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 12 h

Sources & evidence

ORD record
ord-f164953ad6a946a49619469ef1075289
Source dataset
uspto-grants-2012_12
Patent number
US08324250B2

Reaction notes

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