Sodium hydride → 6-(3-Dimethylaminopropyl)-1,9-dimethyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole dihydrochloride

HRID 647947Notes

Reaction equation

HRID 647947 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][N:16]([CH3:18])[CH2:17][C:8]3=1.[H-].[Na+].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][Cl:26]>CN(C)C=O>[ClH:26].[ClH:26].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][N:10]1[C:11]2[C:7](=[C:6]3[C:2]([CH3:1])=[CH:3][S:4][C:5]3=[CH:13][CH:12]=2)[C:8]2[CH2:17][N:16]([CH3:18])[CH2:15][CH2:14][C:9]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 71140Tienocarbine

Product 1

HCID 204843326-(3-Dimethylaminopropyl)-1,9-dimethyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole dihydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.0 g of 1,9-dimethyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole are dissolved in 60 ml of dimethylformamide, 0.78 g of a 50% strength dispersion of NaH is added, whilst stirring, and, after 1 hour, 2.4 g of 3-dimethylaminopropyl chloride are added. After leaving the mixture is stand for 15 hours, the solvent is evaporated off, the residue is taken up in ethyl acetate, the ethyl acetate mixture is washed and dried and the product is purified on SiO2 with chloroform/methanol (1:1). The dihydrochloride is then prepared with isopropyl alcohol/HCl. Melting point: 263° C.

Workup

  1. customAfter leaving the mixture
  2. customfor 15 hours
  3. customthe solvent is evaporated off
  4. washthe ethyl acetate mixture is washed
  5. customdried
  6. customthe product is purified on SiO2 with chloroform/methanol (1:1)
  7. customThe dihydrochloride is then prepared with isopropyl alcohol/HCl

Sources & evidence

ORD record
ord-955e843a4889417c8d3ad22bb3185a4a
Source dataset
uspto-grants-1983_10
Patent number
US04410536

Reaction notes

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