Benzoyl chloride → N-{3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,3,4,5-tetrahydro-8-methyl-5-oxo-2H-[1]benzopyrano[3,4-c]pyridin-9-yl}-benzamide

HRID 1995300Notes

Reaction equation

HRID 1995300 reaction equation
[NH2:1][C:2]1[C:3]([CH3:28])=[CH:4][C:5]2[O:26][C:25](=[O:27])[C:9]3[CH2:10][N:11]([CH2:14][CH2:15][N:16]4[CH2:22][CH:21]5[CH2:23][CH2:24][CH:18]([CH2:19][CH2:20]5)[CH2:17]4)[CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:35](Cl)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(Cl)(Cl)Cl>[CH:21]12[CH2:23][CH2:24][CH:18]([CH2:19][CH2:20]1)[CH2:17][N:16]([CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][C:8]3[C:6]4[CH:7]=[C:2]([NH:1][C:35](=[O:42])[C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:3]([CH3:28])=[CH:4][C:5]=4[O:26][C:25](=[O:27])[C:9]=3[CH2:10]1)[CH2:22]2

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 11430Potassium CarbonateHCID 13189028HCID 13189028, compound

Product 1

HCID 13189030N-{3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,3,4,5-tetrahydro-8-methyl-5-oxo-2H-[1]benzopyrano[3,4-c]pyridin-9-yl}-benzamideYield 38.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 9-amino-3-[2-(3-azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-5H-benzopyrano[3,4-c]pyridin-5-one (2.5 g, 0.007 moles), potassium carbonate (2.4 g, 0.017 moles), and benzoyl chloride (1.0 ml, 0.009 moles) is stirred in chloroform (50 ml) at room temperature. After 24 hours the mixture is poured into ice water. The layers are separated, and the aqueous phase is extracted with chloroform (2×60 ml). The combined organic extracts are washed with brine and dried (magnesium sulfate). The solvent is removed under reduced pressure to leave a syrup, which crystallized from ethyl acetate. Recrystallization gave the product (1.3 g), mp 174°-176° C.

Workup

  1. customThe layers are separated
  2. extractionthe aqueous phase is extracted with chloroform (2×60 ml)
  3. washThe combined organic extracts are washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. customThe solvent is removed under reduced pressure
  6. customto leave a syrup, which
  7. customcrystallized from ethyl acetate
  8. customRecrystallization

Sources & evidence

ORD record
ord-611ef74cdcf8443d93117f3e9dbcb7ea
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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