3-Chloro-N,N-dimethyl-1-propanamine → 9-(3-Dimethylaminopropyl)-1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647944Notes

Reaction equation

HRID 647944 reaction equation
[CH3:1][C:2]1[C:6]2=[C:7]3[C:11](=[CH:12][CH:13]=[C:5]2[S:4][CH:3]=1)[NH:10][C:9]1[CH2:14][CH2:15][NH:16][CH2:17][C:8]3=1.[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22]Cl>CN(C)C=O>[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22][N:16]1[CH2:15][CH2:14][C:9]2[NH:10][C:11]3[C:7]([C:8]=2[CH2:17]1)=[C:6]1[C:2]([CH3:1])=[CH:3][S:4][C:5]1=[CH:13][CH:12]=3

Participants

4

Reactant 2

HCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 20484283HCID 20484283, compound

Product 1

HCID 204843129-(3-Dimethylaminopropyl)-1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

10 g of 1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole, dissolved in 200 ml of dimethylformamide at 90° C., are heated to 90° with a solution of 12 ml of 3-dimethylaminopropyl chloride in 50 ml of dimethylformamide for 3 hours. The reaction mixture is filtered, the filtrate is evaporated and the residue is taken up in chloroform. After washing with water and drying, the organic phase is concentrated, the residue is chromatographed on SiO2 with chloroform/methanol/NH4OH (7:3:0:1) and the product is recrystallised from isopropanol. Melting point: 184° C.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. washAfter washing with water
  4. customdrying
  5. concentrationthe organic phase is concentrated
  6. customthe residue is chromatographed on SiO2 with chloroform/methanol/NH4OH (7:3:0:1)
  7. customthe product is recrystallised from isopropanol

Sources & evidence

ORD record
ord-623cd7677ddf4e8fb8633c361bf4b97d
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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