Sodium Iodide → HCID 14810575, compound

HRID 437384

Reaction equation

HRID 437384 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[CH3:9][C@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([CH3:16])[NH:11]1.[I-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:9][C@H:10]1[CH2:15][CH2:14][CH2:13][C@@H:12]([CH3:16])[N:11]1[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 76612Butanoic acid, 4-chloro-, methyl esterHCID 641768rel-(2R,6S)-2,6-Dimethylpiperidine

Product 1

HCID 14810575HCID 14810575, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 273 g. of methyl 4-chlorobutyrate, 460 g. of cis-2,6-dimethylpiperidine, 10 g. of sodium iodide and 300 ml. of xylene is stirred and heated at reflux for 44 hours, then cooled and filtered. The filter cake is washed with xylene and the combined filtrate and washings are evaporated at reduced pressure to give cis-2,6-dimethyl-1-piperidinebutyric acid, methyl ester which is purified by distillation; b.p. 79°-81° C./0.5 mm.

Workup

  1. additionA mixture of 273 g
  2. temperatureheated
  3. temperatureat reflux for 44 hours
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe filter cake is washed with xylene
  7. customthe combined filtrate and washings are evaporated at reduced pressure

Sources & evidence

ORD record
ord-d2f3b55717314692bbbb371b3e3261ff
Source dataset
uspto-grants-1977_06
Patent number
US04031101

Linked notes

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