Methylamine → 1-(benzo[b]thiophen-7-yl)-N-methylmethanamine

HRID 649004Notes

Reaction equation

HRID 649004 reaction equation
Br[CH2:2][C:3]1[C:8]2[S:9][CH:10]=[CH:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:12][NH2:13]>ClCCl.C(O)C>[S:9]1[CH:10]=[CH:11][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][NH:13][CH3:12])[C:8]1=2

Participants

5

Reactant 2

HCID 6329MethylamineHCID 107517617-(Bromomethyl)-1-benzothiophene

Product 1

HCID 107024531-(benzo[b]thiophen-7-yl)-N-methylmethanamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

7-Bromomethylbenzo[b]thiophene is dissolved in dichloromethane, added to 40 ml of a 33% solution of methylamine in ethanol and allowed to stand overnight. The resulting mixture is concentrated and the residue taken up in dichloromethane and extracted with 2N HCl. The aqueous phase is made strongly basic with NaOH and shaken with dichloromethane. The organic phase is dried with potassium carbonate, concentrated by evaporation and the residue vacuum distilled to produce the title product as an oil. B.p.=103°/1.3 mbar.

Workup

  1. concentrationThe resulting mixture is concentrated
  2. extractionextracted with 2N HCl
  3. dry with materialThe organic phase is dried with potassium carbonate
  4. concentrationconcentrated by evaporation
  5. distillationthe residue vacuum distilled

Sources & evidence

ORD record
ord-8aaa18b0b5a44412abfae50677459ff9
Source dataset
uspto-grants-1988_04
Patent number
US04737516

Reaction notes

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