Toluene → HCID 13092520, compound

HRID 648962Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][C:8](=O)[N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1.B(F)(F)F.CCOCC.C1(C)C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[C:18]([O:19][CH3:20])=[CH:17][C:6]2[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][Cl:15])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Here, 1-(7,8-dimethoxy-1,3,4,5-tetrahydro-2H-3-benzazepin-2-on-3-yl)-3-chloro-propane (1.5 g, 0.005 mol) is dissolved in tetrahydrofuran (20 ml) and, after the addition of boron trifluoride etherate (0.55 ml, 0.0044 mol) and a 2 molar solution of boranedimethylsulfide in toluene (3 ml, 0.006 mol), the mixture is refluxed for 2 hours. Then, further boranedimethylsulfide solution (3 ml) is added and again the mixture is refluxed for 2 hours. After decomposition with methanol the solvents are distilled off and the residue is heated to 100° C. for 10 minutes with semi-concentrated hydrochloric acid (6 ml). The reaction product is extracted with ethyl acetate, the acidic aqueous phase is made alkaline and again extracted with ethyl acetate. The extract is dried, concentrated by evaporation and purified over an aluminium oxide column (activity stage II-III) with methylene chloride.

Workup

temperatureagain the mixture is refluxed for 2 hours
distillationAfter decomposition with methanol the solvents are distilled off
extractionThe reaction product is extracted with ethyl acetate
extractionagain extracted with ethyl acetate
customThe extract is dried
concentrationconcentrated by evaporation
custompurified over an aluminium oxide column (activity stage II-III) with methylene chloride

Sources & evidence

ORD record: ord-7993d08e5ca340ecb582b412c4e0f7c4
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04737495

Reaction notes

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