Methylamine → HCID 20284839, compound
Reaction equation
[CH3:1][NH2:2].[C:3]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[S:9][CH2:8][CH2:7]1)(=O)[CH3:4]>C1C=CC=CC=1.CO>[CH3:1][N:2]=[C:3]([CH:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[S:9][CH2:8][CH2:7]1)[CH3:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of the product (1.70 g) in the above (2) in benzene (36 ml) is added a 30% solution of methylamine in methanol (36 ml). The mixture is heated at 100° C. in a sealed tube for 18 hours and then evaporated to give 4-(1-methyliminoethyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole. The product is dissolved in a mixture of tetrahydrofuran (50 ml) and methanol (50 ml) and sodium borohydride (562 mg) is added thereto with stirring on an ice bath. The mixture is stirred at room temperature for 40 minutes and evaporated. The residue is extracted with ether after addition of some pieces of ice and a 10% aqueous solution of sodium hydroxide. The extract is washed with water, dried and evaporated to give the title compound (1.77 g). Recrystallization from acetone gives colorless prisms melting at 179°-187° C. Yield: 64%.
Workup
- customevaporated
Sources & evidence
- ORD record
- ord-25475b4c4eda45bfa50e5800d6e47dad
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256640
Reaction notes
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