Methylamine → HCID 20284833, compound

HRID 127525Notes

Reaction equation

HRID 127525 reaction equation
[CH:1]([C:3]1([CH3:17])[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH3:16])[C:7]=2[S:6][CH2:5][CH2:4]1)=O.[CH3:18][NH2:19]>C1C=CC=CC=1.CO>[CH3:17][C:3]1([CH:1]=[N:19][CH3:18])[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH3:16])[C:7]=2[S:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 20284774HCID 20284774, compound

Product 1

HCID 20284833HCID 20284833, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of the product (2.0 g) of the above (1) in benzene (20 ml) is added a 30% solution (14 ml) of methylamine in methanol. The solution is stirred for 2 hours and evaporated to give 4,9-dimethyl-4-methyliminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (IR: νmaxCHCl3 1660 cm-1). The product is dissolved in methanol (20 ml) and sodium borohydride (930 mg) is added thereto on ice bath. The mixture is stirred at room temperature for 1 hour and evaporated to remove the solvent. The residue is extracted with ether after addition of some pieces of ice and a 10% aqueous solution of sodium hydroxide. The ethereal extract is again extracted with hydrochloric acid. The extract is made alkaline with an aqueous solution of sodium hydroxide and extracted with ether. The extract is washed with a saline solution, dried and evaporated to give an oil. Crystallization from hydrochloric acid--ethanol gives the hydrochloride (2.06 g) of the title compound melting at 274° C. (decomp.). Yield: 86%.

Workup

  1. customevaporated

Sources & evidence

ORD record
ord-352fd7d311eb43ca848dc2f4dd5f4b8b
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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