Sodium Hydroxide → HCID 12940194, compound

HRID 1659631Notes

Reaction equation

HRID 1659631 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+].[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([Cl:29])=[O:28]>C1C=CC=CC=1>[ClH:29].[CH3:17][O:16][C:14]1[C:13]([O:18][CH3:19])=[CH:12][C:9]2[CH:10]3[N:5]([CH2:6][CH2:7][C:8]=2[CH:15]=1)[CH2:4][CH2:3][CH:2]([NH:1][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([O:23][CH3:22])[CH:25]=1)[CH2:11]3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74374m-Anisoyl chlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940194HCID 12940194, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9, 10-dimethoxy-2H-benzo[a]quinolizine (5 g, 0.019 mole), 150 ml of benzene and 30 ml of 20% NaOH was cooled to below 10° whereupon 3-methoxy benzoyl chloride (3.3 g, 0.02 mole) was added dropwise with stirring. The mixture was stirred in the cold for 1 hour and filtered to remove the solid whereupon the solid was chromatographed over silica gel using benzene-methanol (6:1) as eluant. The major fraction (4.1 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and the solvent was removed in vacuo. The salt was crystallized from methanol-ether to yield 1.5 g of the desired product, m.p. (decomposed at 217°-9°). This compound conforms to Formula II where R1 and R2 are --OCH3R3 is H and R4 is ##STR16##

Workup

  1. additionwas added dropwise
  2. stirringThe mixture was stirred in the cold for 1 hour
  3. filtrationfiltered
  4. customto remove the solid whereupon the solid
  5. customwas chromatographed over silica gel
  6. customthe solvent was removed in vacuo
  7. customThe salt was crystallized from methanol-ether

Sources & evidence

ORD record
ord-4b04b15dc60547fd8811494a8aab3dd8
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

Loading…