Water → Tert-butyl 1-[3-(4-cyanophenoxy)propyl]-4-piperidinylcarbamate

HRID 1591653Notes

Reaction equation

HRID 1591653 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[CH:28][CH:27]=1.O>CN(C)C=O.C(OCC)(=O)C>[C:30]([C:29]1[CH:32]=[CH:33][C:26]([O:25][CH2:24][CH2:23][CH2:22][N:12]2[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:14][CH2:13]2)=[CH:27][CH:28]=1)#[N:31]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 10879224HCID 10879224, compound

Product 1

HCID 23033957Tert-butyl 1-[3-(4-cyanophenoxy)propyl]-4-piperidinylcarbamateYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.44 g of 4-tert-butoxycarbonylaminopiperidine was dissolved in 14 ml of N,N-dimethylformamide. Thereafter, 1.99 g of potassium carbonate and 1.87 g of 4-(3-bromopropoxy)benzonitrile were successively added to the above solution, followed by stirring at room temperature for 24 hours. Water and ethyl acetate were added to the reaction mixture, so that the organic layer was separated. The separated organic layer was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. Thereafter, the solvent was removed under a reduced pressure. The obtained solid was filtrated with a mixed solution consising of n-hexane and diisopropyl ether to obtain 2.12 g of tert-butyl 1-[3-(4-cyanophenoxy)propyl]-4-piperidinylcarbamate.

Workup

  1. customwas separated
  2. washThe separated organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThereafter, the solvent was removed under a reduced pressure
  5. filtrationThe obtained solid was filtrated with a mixed solution consising of n-hexane and diisopropyl ether

Sources & evidence

ORD record
ord-34d304883b254b109aeb0a7cca8057da
Source dataset
uspto-grants-2007_11
Patent number
US07291617B2

Reaction notes

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