Hydrochloric Acid → 2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamine

HRID 1904077Notes

Reaction equation

HRID 1904077 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].[O-]CC.[Na+].Cl.Cl.Cl[CH2:13][C:14]1[CH:19]=[C:18]([CH2:20][N:21]([CH3:23])[CH3:22])[CH:17]=[CH:16][N:15]=1.Cl>C(O)C.O>[CH3:22][N:21]([CH2:20][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([CH2:13][S:5][CH2:4][CH2:3][NH2:2])[CH:19]=1)[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9082Cysteamine HydrochlorideHCID 2723922Sodium ethoxideHCID 132926032-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride

Product 1

HCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamineYield 73.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Cysteamine hydrochloride (3.75 g) was added to a stirred solution of sodium ethoxide (prepared from 2.83 g sodium) in ethanol (200 ml) and the mixture was cooled to less than 10°. 2-Chloromethyl-4-dimethylaminomethylpyridine dihydrochloride (7.3 g) was added portionwise and the solution was stirred for 1 hour. Water (200 ml) was added, the pH was adjusted to ca. 4 with hydrochloric acid and the volume was reduced to ca. 100 ml. The solution was extracted with chloroform, the aqueous phase was basified to pH 12 and extracted with chloroform to give 2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamine (4.7 g) as an oil.

Workup

  1. temperaturethe mixture was cooled to less than 10°
  2. extractionThe solution was extracted with chloroform
  3. extractionextracted with chloroform

Sources & evidence

ORD record
ord-e31a6b66a98548438f2e6b7ad937f186
Source dataset
uspto-grants-1984_03
Patent number
US04439609

Reaction notes

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