Benzoyl chloride → HCID 12940182, compound

HRID 1659641Notes

Reaction equation

HRID 1659641 reaction equation
[NH2:1][CH:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=32)[CH2:4][CH2:3]1.[OH-].[Na+].[C:22]([Cl:30])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1C=CC=CC=1>[ClH:30].[C:22]([NH:1][CH:2]1[CH2:11][CH:10]2[N:5]([CH2:6][CH2:7][C:8]3[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[CH:12][C:9]=32)[CH2:4][CH2:3]1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940182HCID 12940182, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (5.0 g., 0.019 mole), 20% NaOH (25 ml) and 150 ml of benzene was cooled in an ice bath and benzoyl chloride (2.7 g, 0.019 mole) in 10 ml of benzene was added dropwise with stirring. The mixture was stirred in the cold for 30 minutes and at room temperature for 1 hour. The solid was collected, dissolved in chloroform, washed with water, dried (MgSO4) and concentrated in vacuo. The residue (5 g) was chromatographed over silica gel eluting with benzene-methanol (9:1). The free base (3.7 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol and methanol. The solution was concentrated in vacuo and the residue was crystallized from methanol-ether. The resulting solid was recrystallized from ethanol-ether to yield 3.0 g of the desired product, m.p. 250°-1°. This product comforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR36##

Workup

  1. temperaturewas cooled in an ice bath
  2. stirringThe mixture was stirred in the cold for 30 minutes
  3. customThe solid was collected
  4. dissolutiondissolved in chloroform
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue (5 g) was chromatographed over silica gel eluting with benzene-methanol (9:1)
  9. additionThe free base (3.7 g) was converted to the HCl salt with hydrogen chloride in a mixture of 2-propanol and methanol
  10. concentrationThe solution was concentrated in vacuo
  11. customthe residue was crystallized from methanol-ether
  12. customThe resulting solid was recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-15c62f78271a4d1b99fee1dda8764d5f
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

Loading…