Triethylamine → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 1995292Notes

Reaction equation

HRID 1995292 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]2[C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:4]=2[CH:3]=1.C(N(CC)CC)C.Cl.Cl[CH2:29][CH2:30][N:31]1[CH2:37][CH:36]2[CH2:38][CH2:39][CH:33]([CH2:34][CH2:35]2)[CH2:32]1>>[CH:36]12[CH2:38][CH2:39][CH:33]([CH2:34][CH2:35]1)[CH2:32][N:31]([CH2:30][CH2:29][N:14]1[CH2:15][CH2:16][C:11]3[C:5]4[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([CH3:1])=[CH:3][C:4]=4[O:18][C:17](=[O:19])[C:12]=3[CH2:13]1)[CH2:37]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 13136924HCID 13136924, compound

Product 1

HCID 131890193-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 50.7%

Procedure

Prepared by the method described for Example 1 from 1,2,3,4-tetrahydro-8-methyl-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (8.9 g, 0.034 moles), triethylamine (9.5 ml, 0.069 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (7.7 g, 0.034 moles). The product was triturated with 10% aqueous potassium carbonate, filtered off, rinsed with water, and dried to afford the free base. Recrystallization from N,N-dimethylformamide gave the product (7.1 g), mp 187°-188° C.

Workup

  1. customPrepared by the method
  2. customThe product was triturated with 10% aqueous potassium carbonate
  3. filtrationfiltered off
  4. washrinsed with water
  5. customdried
  6. customto afford the free base
  7. customRecrystallization from N,N-dimethylformamide

Sources & evidence

ORD record
ord-0cff21bd7514488f8ab1815c31c9d656
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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