Methyl iodide → HCID 9862160, compound

HRID 1636230Notes

Reaction equation

[CH3:1][C:2]1[S:22][C:5]2[NH:6][C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[CH3:23]N(C)CCN(C)C.C([Li])CCC.CI>O1CCCC1.O>[CH3:1][C:2]1[S:22][C:5]2[N:6]([CH3:23])[C:7]3[CH:21]=[CH:20][CH:19]=[CH:18][C:8]=3[N:9]=[C:10]([N:11]3[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A solution of 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine (3.1 g) (European Patent Publication 0 454 436) in dry tetrahydrofuran (distillated from sodium/benzophenone) was stirred and cooled to -70° C. Tetramethylethylenediamine (1.16 g) was added followed by n-butyllithium (6.25 ml, 0.6M solution), keeping the temperature below -60° C. The deep red solution was stirred for 15 minutes and then methyl iodide (1.42 g) was added. The reaction was allowed to attain room temperature, during which time the red colour discharged. Water was added and the product extracted with ethyl acetate. The solvent was washed with water, dried and evaporated to dryness under reduced pressure. The product was purified by chromatography on Florisil using ethyl acetate as eluent and crystallised from acetronitrile to give the title compound, m.p. 126-128° C.

Workup

customthe temperature below -60° C
customto attain room temperature, during which time
extractionthe product extracted with ethyl acetate
washThe solvent was washed with water
customdried
customevaporated to dryness under reduced pressure
customThe product was purified by chromatography on Florisil
customcrystallised from acetronitrile

Sources & evidence

ORD record: ord-ac9b0307ce7e474cb51aa78797a6e579
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034078

Reaction notes

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