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

HRID 127519Notes

Reaction equation

HRID 127519 reaction equation
[CH:1]([CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[S:6][CH2:5][CH2:4]1)=O.[CH3:22][NH2:23]>C1C=CC=CC=1.CO>[CH3:22][N:23]=[CH:1][CH:3]1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[S:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 202847884-Formyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Product 1

HCID 202848204-Methyliminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-formyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (1.4 g) in absolute benzene (20 ml) is added a 30% solution (1.5 ml) of methylamine in methanol. The mixture is stirred at room temperature for 3 hours and evaporated to give 4-methyliminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole as orange solid. The product is dissolved in a mixture of methanol (20 ml) and tetrahydrofuran (20 ml) and sodium borohydride (274 mg) is added thereto. The mixture is stirred at room temperature for 1 hour and evaporated.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-a7efe45bb36f4d87bde240615936c831
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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