2-Chlorobenzylamine → N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochloride

HRID 1704633Notes

Reaction equation

HRID 1704633 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=O)=O)=CC=1.[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH2:23]>C(#N)C>[ClH:19].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22][NH:23][CH2:11][CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 666482-ChlorobenzylamineHCID 36820342-Thiopheneethanol tosylate

Product 1

HCID 6454011N-((2-chlorophenyl)methyl)thiophene-2-ethylamine hydrochlorideYield 79.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

850 g (3 moles) 2-(2-thienyl)-ethyl paratoluene sulfonate and 850 g (6 moles) ortho-chlorobenzylamine are dissolved in 5.2 liters acetonitrile and the mixture is refluxed during 6.5 hours. After filtration, 630 g ortho-chlorobenzylamine paratoluene sulfonate are removed by filtration. The filtrate is concentrated and the residue is taken up into diisopropyl ether and 500 ml 2N sodium hydroxide. The organic phase is separated and is made acidic with 3N hydrochloric acid. The resulting hydrochloride precipitates out; it is collected by filtration, suction filtered and washed with acetone, to give 684 g (Yield: 78%) N-(2-chloro-benzyl)-2-(2-thienyl)-ethylamine hydrochloride.

Workup

  1. temperaturethe mixture is refluxed during 6.5 hours
  2. filtrationAfter filtration, 630 g ortho-chlorobenzylamine paratoluene sulfonate
  3. customare removed by filtration
  4. concentrationThe filtrate is concentrated
  5. customThe organic phase is separated
  6. customThe resulting hydrochloride precipitates out
  7. filtrationit is collected by filtration, suction
  8. filtrationfiltered
  9. washwashed with acetone

Sources & evidence

ORD record
ord-c815c6c0d8484f97a7e57300f768adb0
Source dataset
uspto-grants-1978_11
Patent number
US04127580

Reaction notes

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