Benzoyl chloride → HCID 12940182, compound

HRID 1659629Notes

Reaction equation

HRID 1659629 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 g, 0.019 mole), 150 ml of benzene and 25 ml of 20% NaOH was cooled in an ice bath, and a solution of 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 over MgSO4 and concentrated in vacuo to leave a solid residue. The solid was crystallized from acetone-petroleum ether and chromatographed over silica gel using benzene-MeOH (9:1) as the eluant. The major fraction (3.9 g) was converted to the HCl salt with hydrogen chloride in 2-propanol, and concentrated in vacuo to isolate the salt. The salt was crystallized from methanol-ether and again from absolute ethanol-ether to yield 3.0 g of the desired product, m.p. (decomposed at 250°-1°). This compound conforms with Formula II where R1 and R2 are OCH3, R3 is H and R4 is phenyl.

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 over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto leave a solid residue
  9. customThe solid was crystallized from acetone-petroleum ether
  10. customchromatographed over silica gel
  11. concentrationconcentrated in vacuo
  12. customto isolate the salt
  13. customThe salt was crystallized from methanol-ether and again from absolute ethanol-ether

Sources & evidence

ORD record
ord-d4e1686b30cd4c18ae4b139d931974b5
Source dataset
uspto-grants-1981_12
Patent number
US04304913

Reaction notes

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