3-Bromo-1-propanol → cis-2,6-Dimethyl-1-piperidinepropanol

HRID 1763484Notes

Reaction equation

HRID 1763484 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.Br[CH2:10][CH2:11][CH2:12][OH:13]>C1(C)C(C)=CC=CC=1>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([CH3:8])[N:3]1[CH2:10][CH2:11][CH2:12][OH:13]

Participants

4

Reactant 2

HCID 123083-Bromo-1-propanolHCID 641768rel-(2R,6S)-2,6-Dimethylpiperidine

Product 1

HCID 13239624cis-2,6-Dimethyl-1-piperidinepropanol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution of 460 g. of cis-2,6-dimethylpiperidine in 300 ml. of xylene is treated with 278 g. of 3-bromopropanol over a period of 15 minutes. The mixture is stirred and heated at reflux for 2 hours, then allowed to cool while stirring for 16 hours. The mixture is filtered and the filtrate evaporated at reduced pressure. The residue is distilled at reduced pressure to give cis2,6-dimethyl-1-piperidinepropanol; b.p. 147°-149° C./25 mm.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. stirringwhile stirring for 16 hours
  5. filtrationThe mixture is filtered
  6. customthe filtrate evaporated at reduced pressure
  7. distillationThe residue is distilled at reduced pressure

Sources & evidence

ORD record
ord-7eeb5c7401e34282b2def1f34e0b0711
Source dataset
uspto-grants-1978_09
Patent number
US04112103

Reaction notes

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