Hydrochloric Acid → HCID 86626017, compound

HRID 870364Notes

Reaction equation

HRID 870364 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:14][C@@H:13]3[C@H:8]([CH2:9][CH2:10][CH2:11][N:12]3[C:15](=[O:18])[CH2:16][CH3:17])[CH2:7][C:6]=2[CH:19]=1.[CH:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])[CH3:21].Cl.C(OCC)C>N1C=CC=CC=1>[CH:20]([C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:14][C@@H:13]4[C@H:8]([CH2:9][CH2:10][CH2:11][N:12]4[C:15](=[O:18])[CH2:16][CH3:17])[CH2:7][C:6]=3[CH:19]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 27348824-(Propan-2-yl)benzene-1-sulfonyl chlorideHCID 86626018HCID 86626018, compound

Product 1

HCID 86626017HCID 86626017, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.21 g of trans-1-(7-amino-3,4,4a,5,10,10a-hexahydro-2H-benzo[g]quinolin-1-yl)propan-1-one (0.38 mmol) were dissolved in 2 ml of pyridine. At 0-4° C., 0.08 g of 4-isopropyl-benzene sulfonylchloride (0.4 mmol) were added, and the reaction stirred for 1 h under cooling. 40 ml of aqueous 1 N hydrochloride acid and diethyl ether were added, the phases separated, and the aqueous layer extracted twice with diethyl ether. The organic phases were combined, washed three times with water acidified with 1 N aqueous hydrochloric acid, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure to yield 0.118 g of the product.

Workup

  1. temperatureunder cooling
  2. customthe phases separated
  3. extractionthe aqueous layer extracted twice with diethyl ether
  4. washwashed three times with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-533a06f142474440a07fee9071e55fd0
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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