Hydrochloric Acid → HCID 11640438, compound

HRID 870362Notes

Reaction equation

HRID 870362 reaction equation
[CH2:1]([N:4]1[C@@H:13]2[C@H:8]([C:9]3[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([CH3:21])[CH3:20].Cl>N1C=CC=CC=1.ClCCl.C(OCC)(=O)C>[CH2:1]([N:4]1[C@@H:13]2[C@H:8]([C:9]3[CH:17]=[CH:16][C:15]([NH:18][S:28]([C:25]4[CH:26]=[CH:27][C:22]([CH:19]([CH3:21])[CH3:20])=[CH:23][CH:24]=4)(=[O:30])=[O:29])=[CH:14][C:10]=3[CH2:11][CH2:12]2)[CH2:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 68911690HCID 68911690, compound

Product 1

HCID 11640438HCID 11640438, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
5 °C

Procedure

(4aS,10bS)-4-Allyl-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinolin-8-ylamine (60 mg, 0.23 mmol) was dissolved in pyridine-dichloromethane (1:2, 7.5 mL) and cooled to 5° C. 4-Isopropylbenzenesulfonyl chloride (50 mg, 0.24 mmol) was added and the solution stirred at 5° C. for 3 h. Solution was evaporated, partitioned between ethyl acetate and water, and the organic phase separated and dried over MgSO4. The filtered solution was concentrated and separated by column chromatography (dichloromethane-3% MeOH) to give an oil. The oil was dissolved in ethyl acetate and HCl (4M, dioxane) was added to give the product as a white solid (20 mg, 15%).

Workup

  1. customSolution was evaporated
  2. custompartitioned between ethyl acetate and water
  3. customthe organic phase separated
  4. dry with materialdried over MgSO4
  5. concentrationThe filtered solution was concentrated
  6. customseparated by column chromatography (dichloromethane-3% MeOH)
  7. customto give an oil

Sources & evidence

ORD record
ord-500643a4df2941a4a325917f8c98c7fb
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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