Hexamethylphosphoramide → 9-[4,4-Bis(4-fluorophenyl)butyl]-1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole

HRID 647943Notes

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.CN(C)P(=O)(N(C)C)N(C)C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]([C:41]2[CH:46]=[CH:45][C:44]([F:47])=[CH:43][CH:42]=2)[CH2:37][CH2:38][CH2:39]I)=[CH:32][CH:31]=1>CN(C)C=O>[F:29][C:30]1[CH:31]=[CH:32][C:33]([CH:36]([C:41]2[CH:42]=[CH:43][C:44]([F:47])=[CH:45][CH:46]=2)[CH2:37][CH2:38][CH2:39][N:16]2[CH2:15][CH2:14][C:9]3[NH:10][C:11]4[C:7]([C:8]=3[CH2:17]2)=[C:6]2[C:2]([CH3:1])=[CH:3][S:4][C:5]2=[CH:13][CH:12]=4)=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 80 °C

Procedure

2.4 g of 1-methyl-7,8,9,10-tetrahydrothieno[3,2-e]pyrido[4,3-b]indole are dissolved in 50 ml of dimethylformamide and 10 ml of hexamethylphosphoric acid triamide 4.5 g of 4,4-bis-(4-fluorophenyl)butyl iodide are added and the mixture is warmed to 80° C. under N2 for 5 hours. The solvent is then evaporated off; the residue is taken up in chloroform, the chloroform mixture is washed with water, dried and evaporated, the residue is chromatographed on Al2O3 with chloroform and the product is recrystallised from isopropanol. Melting point: 158° C.

Workup

customThe solvent is then evaporated off
washthe chloroform mixture is washed with water
customdried
customevaporated
customthe residue is chromatographed on Al2O3 with chloroform
customthe product is recrystallised from isopropanol

Sources & evidence

ORD record: ord-9796215c75ee4e54a3d5f7f3e8b9bb95
Source dataset: uspto-grants-1983_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04410536

Reaction notes

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