Sodium hydride → HCID 20306014, compound

HRID 1732348Notes

Reaction equation

HRID 1732348 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH2:16]>CN(C)C=O.O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:16][C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH2:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 107492911-(4-Hydroxypiperidin-1-yl)ethan-1-one

Product 1

HCID 20306014HCID 20306014, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

N-Acetyl-4-hydroxypiperidine (13.6 g.) in dimethylformamide (50 ml.) was added dropwise to a stirred suspension of sodium hydride (10 g. 50% dispersion in mineral oil) in dimethylformamide (50 ml.) under nitrogen. The mixture was stirred at room temperature for 3 hours then α-(bromomethyl)styrene (20 g.) in dimethylformamide (50 ml.) was added dropwise. The mixture was stirred at room temperature for 4 hours, then diluted with water and extracted with chloroform (3×200 ml.). The combined chloroform extracts were dried (Na2SO4), evaporated in vacuo, and distilled to give N-acetyl-4-(2-phenylallyloxy)piperidine (25 g.), b.p. 170°-180° C./0.3 mm. with an n.m.r. spectrum in accordance with this structure.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. extractionextracted with chloroform (3×200 ml.)
  3. dry with materialThe combined chloroform extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. distillationdistilled

Sources & evidence

ORD record
ord-4a43641a25d943c284d24cd6cf6312f7
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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