RU 25591 → HCID 21153170, compound

HRID 1447650Notes

Reaction equation

HRID 1447650 reaction equation
[CH3:1][N:2]([CH3:24])[C@@H:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[C@H:5]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=2)[CH2:4]1>C(O)C.[H][H].[Pt](=O)=O>[CH3:1][N:2]([CH3:24])[C@@H:3]1[CH2:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[C@H:5]([O:14][C:15]2[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:4]1

Participants

5

Reactant 1

HCID 182578RU 25591

Product 1

HCID 21153170HCID 21153170, compoundYield 107.1%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

370 mg of platinum dioxide were added to a solution of 3.7 g of cis N,N-dimethyl-5-[4-nitrophenoxy]-6,7,8,9-tetrahydro-benzocycloheptene-7-amine in 200 ml of ethanol and one liter of hydrogen was bubbled therethrough for 30 minutes with stirring. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure to obtain 3.6 g of cis N,N-dimethyl-5-[4-aminophenoxy]-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-amine in the form of an orange oil. The said oil was dissolved in 20 ml of ethyl acetate and a solution of ethyl acetate saturated with gaseous hydrogen chloride was added thereto to adjust the pH to 1. The mixture stood for one hour at room temperature and was then vacuum filtered to obtain 4.1 g of the dihydrochloride of the cis compound in the form of colorless crystals melting at ≈260° C.

Workup

  1. customwas bubbled
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d72f181dd1b04766b1328306636529e8
Source dataset
uspto-grants-1979_12
Patent number
US04177292

Reaction notes

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