p-Anisoyl chloride → HCID 12940186, compound

HRID 1659630Notes

Reaction equation

HRID 1659630 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:32]=[CH:31][C:27]([C:28]([Cl:30])=[O:29])=[CH:26][CH:25]=1>C1C=CC=CC=1>[ClH:30].[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:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[CH2:11]3

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 14798Sodium HydroxideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940186HCID 12940186, compoundYield 9.7%

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 g, 0.019 mole), 200 ml of benzene and 25 ml of 20% NaOH was cooled 10° and a solution of 4-methoxy benzoyl chloride (3.3 g, 0.019 mole) in 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 after removal of the solvent and chromatographed over silica gel using benzene-methanol (6:1) as eluant. The major fraction (3.8 g) was converted to the HCl salt with hydrogen chloride in 2-propanol. The solvent was removed from the salt in vacuo whereupon the salt was twice recrystallized from methanol-ether, once from 2-propanol and again from absolute ethanol-ethyl acetate to yield 0.8 g of the desired product m.p. (decomposed at 244°-6°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR14##

Workup

  1. temperaturewas cooled 10°
  2. stirringThe mixture was stirred in the cold for 30 minutes
  3. customThe solid was collected
  4. customafter removal of the solvent
  5. customchromatographed over silica gel
  6. customThe solvent was removed from the salt in vacuo whereupon the salt
  7. customwas twice recrystallized from methanol-ether, once from 2-propanol and again from absolute ethanol-ethyl acetate

Sources & evidence

ORD record
ord-b37183c13429419982a531b824c990e6
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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