Methyl Bromide → HCID 69958772, compound

HRID 893859Notes

Reaction equation

HRID 893859 reaction equation
[ClH:1].[S:2]1[C:6]23[CH:14]=[CH:13][CH:12]=[CH:11][C:7]2=[N:8][CH2:9][CH2:10][CH:5]3[CH:4]([C:15]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:16])[CH2:3]1.[CH2:23](N(CC)CC)C.CBr>C(Cl)(Cl)Cl>[ClH:1].[CH3:23][CH:3]1[S:2][C:6]23[CH:14]=[CH:13][CH:12]=[CH:11][C:7]2=[N:8][CH2:9][CH2:10][CH:5]3[CH:4]1[C:15]([N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1)=[O:16]

Participants

5

Reactant 3

HCID 6323Methyl BromideHCID 8471TriethylamineHCID 19891183HCID 19891183, compound

Product 1

HCID 69958772HCID 69958772, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 5 ml of chloroform were dissolved 0.34 g of 4-(1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carbonyl)morpholine hydrochloride, 0.31 ml of triethylamine, and 0.11 g of methyl bromide, and the solution was refluxed for 30 minutes. Chloroform was distilled off under reduced pressure, 20 ml of an aqueous 5% sodium hydrogencarbonate solution and 50 ml of ethyl acetate were added to the residue, and the ethyl acetate layer was washed with a saturated sodium chloride solution and dried by sodium sulfate. Then, ethyl acetate was distilled under reduced pressure and the residue was purified by silica gel thin layer chromatography. Then, 1 ml of a mixture of 1N hydrochloric acid in ethyl acetate was added to the residue and crystals deposited were collected by filtration to provide 0.29 g (yield of 82%) of 4-(2 -methyl-1,2,3,4-tetrahydrobenzo[b]thieno[2,3-c]pyridine-3-carbonyl)morpholine.hydrochloride.

Workup

  1. temperaturethe solution was refluxed for 30 minutes
  2. distillationChloroform was distilled off under reduced pressure, 20 ml of an aqueous 5% sodium hydrogencarbonate solution and 50 ml of ethyl acetate
  3. additionwere added to the residue
  4. washthe ethyl acetate layer was washed with a saturated sodium chloride solution
  5. dry with materialdried by sodium sulfate
  6. distillationThen, ethyl acetate was distilled under reduced pressure
  7. customthe residue was purified by silica gel thin layer chromatography
  8. additionThen, 1 ml of a mixture of 1N hydrochloric acid in ethyl acetate was added to the residue and crystals
  9. filtrationdeposited were collected by filtration

Sources & evidence

ORD record
ord-f981fb75cd7a4ad29a2656249c2b5e54
Source dataset
uspto-grants-1992_06
Patent number
US05126448

Reaction notes

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