Lithium hydroxide, monohydrate → HCID 23702578, compound

HRID 1906165Notes

Reaction equation

HRID 1906165 reaction equation
[CH2:1]([N:4]1[CH2:14][CH2:13][CH2:12][CH:6]([C:7]([O:9]CC)=[O:8])[CH2:5]1)[CH2:2][CH3:3].O.[OH-].[Li+:17]>C(O)C>[CH2:1]([N:4]1[CH2:14][CH2:13][CH2:12][CH:6]([C:7]([O-:9])=[O:8])[CH2:5]1)[CH2:2][CH3:3].[Li+:17]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 13905178Ethyl 1-propylpiperidine-3-carboxylate

Product 1

HCID 23702578HCID 23702578, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl N-propylnipecotate (73.86 g) was dissolved in 500 ml ethanol, treated with lithium hydroxide monohydrate (15.57 g) at reflux for 24 hours. Upon evaporation and drying in vacuo (100° C., eight hours), lithium N-propylnipecotate was obtained (white powder; 60 g). A solution of 17.7 g of this salt in 200 ml THF was treated dropwise with one equivalent of methyl-lithium, at 0° C. After stirring at room temperature overnight, an aqueous work-up yielded 3-acetyl-N-propylpiperidine (mp of HCl salt 108°-111° C.). When 2.5 of this compound were intimately mixed with 2.28 g of thiourea and 3.81 g of iodine and heated on a steam bath for 24 hours, followed by a column chromatography (Silica; acetone) and salt formation by the procedure of Example 2, 1.75 g of 4-(1-propyl-3-piperidyl)-2-thiazolamine hydrochloride (mp 243°-248° C.) were obtained.

Workup

  1. temperatureat reflux for 24 hours
  2. customUpon evaporation
  3. customdrying in vacuo (100° C., eight hours)

Sources & evidence

ORD record
ord-ff35f3dfe4554896b88902221a640173
Source dataset
uspto-grants-1987_03
Patent number
US04650805

Reaction notes

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