Methylamine → 4-Methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

HRID 127515

Reaction equation

HRID 127515 reaction equation
[CH:1]([CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[S:6][CH2:5][CH2:4]1)=O.[CH3:16][NH2:17].[BH4-].[Na+]>CO>[CH3:16][NH:17][CH2:1][CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[S:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 147356294-Formyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Product 1

HCID 30560964-Methylaminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoleYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of the product of the above (2) (2.17 g) in absolute methanol (10 ml) is added a 30% solution (2.2 ml) of methylamine in methanol. The mixture is stirred at room temperature for 1 hour. Sodium borohydride (380 mg) is added to the filtrate. The mixture is stirred at room temperature for 2 hours and evaporated to remove the solvent. The residue is acidified with 2 N hydrochloric acid after addition of water. The solution is extracted with chloroform to remove neutral impurities. The aqueous layer is made alkaline with an aqueous solution of sodium hydroxide and extracted again with chloroform. The extract is washed with water, dried and evaporated to remove the solvent. The residue is treated with small amount of benzene to give the 1/6 benzene adduct (2.21 g) of the title compound melting at 78°-81° C. Yield: 90%

Workup

  1. stirringThe mixture is stirred at room temperature for 2 hours
  2. customevaporated
  3. customto remove the solvent
  4. additionafter addition of water
  5. extractionThe solution is extracted with chloroform
  6. customto remove neutral impurities
  7. extractionextracted again with chloroform
  8. washThe extract is washed with water
  9. customdried
  10. customevaporated
  11. customto remove the solvent
  12. additionThe residue is treated with small amount of benzene

Sources & evidence

ORD record
ord-7aefcbef30b7468589aab25cc4c62a5a
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Linked notes

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