Piperidine → 11-(Piperidin-1-yl)undecan-1-ol

HRID 36760

Reaction equation

HRID 36760 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Br.N1CCCCC1>>[OH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 7416311-Bromo-1-undecanolHCID 203244Piperidine, hydrobromide (1:1)

Product 1

HCID 312228311-(Piperidin-1-yl)undecan-1-olYield 96.3%

Procedure

11-Bromoundecanol (11.00 g., 43.79 mmole) was dissolved in 100 ml. of piperidine and heated at reflux temperature for 18 hours. The reaction mixture was allowed to cool and most of the precipitated piperidine hydrobromide was removed by filtration. The excess piperidine is removed by simple distillation and the resultant solid residue is recrystallized from ethanol and water. After drying, 10.78 g. (96.3% yield) of 1-hydroxy-11-(N-piperidyl)undecane was obtained. m.p. 62°-65° C., 1H-NMR (200 MHz, CDCl3) δ=1.2-1.7 ppm, m, 24H; 2.10, broad s, 1H; 2.20-2.45, m, 6H; 3.63, t, 2H.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customwas removed by filtration
  3. customThe excess piperidine is removed by simple distillation
  4. customthe resultant solid residue is recrystallized from ethanol and water
  5. customAfter drying

Sources & evidence

ORD record
ord-5196aa637c7740218f9e817e1b948708
Source dataset
uspto-grants-1995_05
Patent number
US05416210

Linked notes

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