4-Toluenesulfonyl chloride → HCID 19848776, compound

HRID 1905131Notes

Reaction equation

C[O:2]C1C=C(CNCCCNCCCCNCCCN)C=CC=1O.O[N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36]([CH3:44])([CH3:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:34]=2)[CH2:29][CH:28]([CH2:45][CH2:46][NH2:47])[C:27]1([CH3:49])[CH3:48].C(N(CC)CC)C.[C:57]1([CH3:67])[CH:62]=[CH:61][C:60]([S:63](Cl)(=[O:65])=[O:64])=[CH:59][CH:58]=1>C(Cl)Cl>[OH:2][C:31]1[CH:32]=[C:33]([C:36]([CH3:44])([CH3:43])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:34]=[C:35]2[C:30]=1[CH2:29][CH:28]([CH2:45][CH2:46][NH:47][S:63]([C:60]1[CH:61]=[CH:62][C:57]([CH3:67])=[CH:58][CH:59]=1)(=[O:65])=[O:64])[C:27]([CH3:49])([CH3:48])[NH:26]2

Participants

Conditions

Temperature: -20 °C

Procedure

To 20 ml of methylene chloride is added 346 mg (1 mmole) dl-5-hydroxy-3-(2-aminoethyl)-7-(1,1-dimethylheptyl)-2,2-dimethyl-1,2,3,4-tetrahydroquinoline and 0.166 ml (1.2 mmole) triethylamine. The solution is cooled to -20° C. and a solution of ;b 191 mg (1 mmole) p-toluenesulfonyl chloride in 10 ml methylene chloride is added dropwise over ten minutes. The mixture is allowed to warm to 0° C., poured into ice/water and the layers separated. The aqueous layer is extracted with fresh methylene chloride, the combined organic layers washed with water, saturated sodium bicarbonate solution, brine and dried over anhydrous magnesium sulfate. Evaporation of solvent affords the crude product which is purified by chromatography on silica gel.

Workup

temperatureto warm to 0° C.
customthe layers separated
extractionThe aqueous layer is extracted with fresh methylene chloride
washthe combined organic layers washed with water, saturated sodium bicarbonate solution, brine
dry with materialdried over anhydrous magnesium sulfate
customEvaporation of solvent

Sources & evidence

ORD record: ord-13641822dfc14c72ab80cc3d0118b245
Source dataset: uspto-grants-1989_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04841078

Reaction notes

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