Acetic Acid → N,N-Dimethyl-1-(2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-yl)methanamine

HRID 127512Notes

Reaction equation

HRID 127512 reaction equation
NCC1[C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]=2[S:6]CC1.C(O)(=O)C.[CH2:20]=O.[C:22]([BH3-])#[N:23].[Na+].O1[CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH3:20][N:23]([CH2:27][CH:28]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][CH2:30][CH2:29]1)[CH3:22]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 30560881-(2,3,4,9-Tetrahydrothiopyrano[2,3-b]indol-4-yl)methanamineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 3056094N,N-Dimethyl-1-(2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-4-yl)methanamineYield 66%

Procedure

To a solution of 4-aminomethyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (1.8 g) in tetrahydrofuran (80 ml) are added acetic acid (2.3 ml), 37% formalin (5.6 ml) and sodium cyanoborohydride (1.35 g) successively. 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 an 10% aqueous solution of sodium hydroxide. The extract is washed with water, dried and evaporated to give an oil (3 g). The oil is chromatographed on a column of basic alumina (70 g) and eluted with ethyl acetate-hexane (1:1). The eluate is evaporated to give crystals of the title compound (1.34 g) melting at 121°-122° C. Yield: 66%

Workup

  1. customevaporated
  2. customto remove the solvent
  3. extractionThe residue is extracted with ether
  4. additionafter addition of some pieces of ice
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-9fbfb24f88004a528058fc4d373d827d
Source dataset
uspto-grants-1981_03
Patent number
US04256640

Reaction notes

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