Methyl iodide → 4-(diphenylmethyl)-1-N-(n-dodecyliminomethyl)piperidine fumarate

HRID 1413950Notes

Reaction equation

HRID 1413950 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH:14]=S)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CI.[CH2:24]([NH2:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].[OH-].[Na+].[C:39]([O-:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([O-:44])=[O:43]>C(Cl)(Cl)Cl>[C:39]([OH:46])(=[O:45])/[CH:40]=[CH:41]/[C:42]([OH:44])=[O:43].[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:8]2[CH2:13][CH2:12][N:11]([CH:14]=[N:36][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 6328Methyl iodideHCID 13583DodecylamineHCID 14798Sodium HydroxideHCID 5460307FumarateHCID 130978784-(Diphenylmethyl)-1-piperidinecarbothioaldehyde

Product 1

HCID 202912264-(diphenylmethyl)-1-N-(n-dodecyliminomethyl)piperidine fumarate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5.54 g (0.019 mole) of 4-(diphenylmethyl)-1-piperidinecarbothioaldehyde in 20 ml of chloroform was treated with 2.65 g (1.16 ml, 0.019 mole) of methyl iodide and refluxed for one hour. The resulting solution was treated with 3.49 g (0.019 mole) of n-dodecylamine, refluxed one and one half hours, cooled, treated with aqueous sodium hydroxide and the organic layer separated. After drying, evaporation yielded an oil which was converted to the fumarate to yield 4-(diphenylmethyl)-1-N-(n-dodecyliminomethyl)piperidine fumarate; m.p. 143°-145.5° C.

Workup

  1. temperaturerefluxed for one hour
  2. temperaturerefluxed one and one half hours
  3. temperaturecooled
  4. customthe organic layer separated
  5. customAfter drying
  6. customevaporation
  7. customyielded an oil which

Sources & evidence

ORD record
ord-0d6cffce02a649ea93587ddd40a8a621
Source dataset
uspto-grants-1981_02
Patent number
US04251655

Reaction notes

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