Water → HCID 22254653, compound

HRID 1611665Notes

Reaction equation

HRID 1611665 reaction equation
[C:1]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:15]1([CH:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:22][CH2:23]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:4]([O:3][C:1]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:23][CH2:22][CH:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:11][CH2:10]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 883331,1'-(3-Bromopropylidene)bisbenzeneHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 22254653HCID 22254653, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(Boc-amino) piperidine (10 g, 50 mmol) in acetonitrile (200 ml) was added 3,3-diphenylpropyl bromide (15.1 g, 55 mmol), tetra-butylammonium iodide (2 g, 5 mmol) and potassium carbonate (15 g, 100 mmol) and the mixture refluxed. After 5 h the reaction mixture was cooled and poured into water. The solution was partitioned with EtOAc and the organic layer dried (MgSO4), concentrated and purified by column chromatography (toluene: EtOAc, 1:1 with 1% triethylamine) to give the title compound as an oil (15.9 g, 40 mmol); MS: 395.

Workup

  1. temperaturethe mixture refluxed
  2. temperatureAfter 5 h the reaction mixture was cooled
  3. customThe solution was partitioned with EtOAc
  4. dry with materialthe organic layer dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography (toluene: EtOAc, 1:1 with 1% triethylamine)

Sources & evidence

ORD record
ord-c50c621041d9406b83c2c1aef5b12198
Source dataset
uspto-grants-2006_01
Patent number
US06989393B2

Reaction notes

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