Potassium Carbonate → HCID 66841294, compound

HRID 1928992Notes

Reaction equation

HRID 1928992 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].O[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1.CCN(C(C)C)C(C)C.[I-].C(C[P+](C)(C)C)#N.C(=O)([O-])[O-].[K+].[K+]>C(#N)CC.O.C(Cl)Cl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidineHCID 10514344(Cyanomethyl)trimethylphosphanium iodide2×HCID 147994684-Hydroxy-1-piperidineethanol

Product 1

HCID 66841294HCID 66841294, compoundYield 84.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 7854PropionitrileSolvent

Procedure

Piperidin-4-yl-carbamic acid tert-butyl ester 3 (5 g, 25 mmol), 1-(2-Hydroxy-ethyl)-piperidin-4-ol 22 (4 g, 27.5 mmol) and DIEA (5.6 ml, 32.5 mmol) are suspended in 25 ml of propionitril. Cyanomethyl-trimethyl-phosphonium iodide (4 g, 30 mmol) is added and the reaction mixture is refluxed. Additional portions of cyanomethyl-trimethyl-phosphonium iodide (1.5 g, 11.25 mmol) are added after 90 minutes and after 3 hours. After cooling to room temperature, a solution of potassium carbonate (4 g) in 250 ml of water is added and the product is isolated by extraction with DCM. Evaporation under reduced pressure gave 6.9 g of a red oil which could be crystallized from ether.

Workup

  1. temperaturethe reaction mixture is refluxed
  2. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-18fcc47f8e02424bab08959ee0d884ef
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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