Sodium Hydroxide → HCID 12940210, compound

HRID 1659637Notes

Reaction equation

HRID 1659637 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:29]=[CH:28][C:27]([CH2:30][C:31]([Cl:33])=[O:32])=[CH:26][CH:25]=1>C1(C)C=CC=CC=1>[ClH:33].[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:31](=[O:32])[CH2:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][CH:26]=1)[CH2:11]3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 27346884-Methoxyphenylacetyl chlorideHCID 13074442HCID 13074442, compound

Product 1

HCID 12940210HCID 12940210, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a cold mixture of 2-amino-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizine (7.3 g, 0.029 mole), 200 ml of toluene and 50 ml of 20% NaOH was added dropwise 5.5 g of 4-methoxyphenylacetyl chloride. The resulting mixture was stirred in the cold for 1 hour whereupon the solid product was collected by filtration and chromatographed over silica gel using ethyl acetate-methanol (3:1) as eluant. The major fraction (3.4 g) was converted to the HCl salt with hydrogen chloride in 2-propanol and concentrated by removal of the solvent in vacuo. The concentrate was crystallized from methanol-ether and recrystallized from methanol-ether to yield 2.2 g of the desired product, m.p. (decomposed at 188°-90°). This compound conforms to Formula II where R1 and R2 are --OCH3, R3 is H and R4 is ##STR24##

Workup

  1. filtrationwas collected by filtration
  2. customchromatographed over silica gel
  3. concentrationconcentrated by removal of the solvent in vacuo
  4. customThe concentrate was crystallized from methanol-ether
  5. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-bd7b8ef17cf24326a6c42f59e12c64bb
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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