Potassium Carbonate → HCID 67849038, compound

HRID 2380217Notes

Reaction equation

HRID 2380217 reaction equation
[N:1]1([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:18])([CH3:17])[CH2:9][NH:8]2)[CH2:5][CH:4]=[CH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:27]=[C:28]([CH2:33][C:34](Cl)=[O:35])[CH:29]=[CH:30][C:31]=1[Cl:32].Cl.C(OCC)C>C(Cl)(Cl)Cl.C(OCC)(=O)C>[ClH:25].[N:1]1([CH2:6][C:7]2([C:34](=[O:35])[CH2:33][C:28]3[CH:29]=[CH:30][C:31]([Cl:32])=[C:26]([Cl:25])[CH:27]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([CH3:18])([CH3:17])[CH2:9][NH:8]2)[CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 27581492-(3,4-Dichlorophenyl)acetyl chlorideHCID 10953452Ether hydrochlorideHCID 15020434HCID 15020434, compound

Product 1

HCID 67849038HCID 67849038, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

Prepared as Example No. 1 from 1.4 g (5.78 mmoles) of 1-(3-pyrrolin-1-yl)methyl-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline, 1.6 g (11.59 moles) of anhydrous potassium carbonate and 1.5 g (6.71 moles) of 3,4-dichlorophenylacetyl chloride in 50 ml of dry chloroform. The work-up of the reaction mixture afforded 1.9 g of the crude product which was dissolved in 60 ml of ethyl acetate and the solution brought to acidic pH with HCl/diethyl ether. The precipitate was filtered, washed and dried, to yield 1.6 g of the title compound. C24H26Cl2N2O.HCl M.P.=254°-257° C. M.W.=465.843 Elemental analysis: Calcd. C,61.87; H,5.84; N,6.01; Cl,22.83; Found C,61.94; H,5.88; N,5.99; C1,22.75. I.R. (KBr): 3450; 2960; 2540; 1630; 1440 cm-1N.M.R. (CDCl3): δ12.5 (s, broad, 1H); 6.9-7.5 (m, 7H); (80 MHz) 6.1 (dd, 1H); 5.8 (s, 2H); 3.9-5.1 (m, 4H);

Workup

  1. customThe work-up of the reaction mixture afforded 1.9 g of the crude product which
  2. filtrationThe precipitate was filtered
  3. washwashed
  4. customdried

Sources & evidence

ORD record
ord-7737578fd04e48ea8a61c73beb5099b0
Source dataset
uspto-grants-1994_11
Patent number
US05366981

Reaction notes

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