Cysteamine Hydrochloride → 2-(2-Aminoethylthiomethyl)-4-methoxypyridine dihydrochloride

HRID 262467Notes

Reaction equation

HRID 262467 reaction equation
[ClH:1].[NH2:2][CH2:3][CH2:4][SH:5].[Na].Cl.[Cl:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=1>C(O)C.CO>[ClH:8].[ClH:1].[NH2:2][CH2:3][CH2:4][S:5][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 5360545SodiumHCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochloride

Product 1

HCID 204742322-(2-Aminoethylthiomethyl)-4-methoxypyridine dihydrochlorideYield 77.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Cysteamine hydrochloride (7.62 g) was added to a solution of sodium (4.70 g) in ethanol (170 cc) and the mixture was stirred and cooled to 10° and 2-chloromethyl-4-methoxypyridine hydrochloride (11.5 g) in methanol (50 cc) was added over 35 minutes, and the mixture was left overnight at room temperature. The mixture was filtered and the filtrate was evaporated to a residue which was partitioned between chloroform and water. The chloroform extract was evaporated to an oil which was crystallised from 2.1 M ethanolic hydrogen chloride to give 2-(2-aminoethylthiomethyl)-4-methoxypyridine dihydrochloride (12.4 g) m.p. 172.5° (decomp).

Workup

  1. temperaturecooled to 10°
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to a residue which
  4. customwas partitioned between chloroform and water
  5. extractionThe chloroform extract
  6. customwas evaporated to an oil which
  7. customwas crystallised from 2.1 M ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-4148594f0b4d440db3a428a9c6031bf7
Source dataset
uspto-grants-1979_05
Patent number
US04154838

Reaction notes

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