Triethylamine → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8,9,10-trimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochloride

HRID 1995298Notes

Reaction equation

HRID 1995298 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[C:7]2[C:14]3[CH2:19][CH2:18][NH:17][CH2:16][C:15]=3[C:20](=[O:22])[O:21][C:6]=2[CH:5]=1.C(N(CC)CC)C.Cl.[Cl:31][CH2:32][CH2:33][N:34]1[CH2:40][CH:39]2[CH2:41][CH2:42][CH:36]([CH2:37][CH2:38]2)[CH2:35]1>>[ClH:31].[CH:39]12[CH2:41][CH2:42][CH:36]([CH2:37][CH2:38]1)[CH2:35][N:34]([CH2:33][CH2:32][N:17]1[CH2:18][CH2:19][C:14]3[C:7]4[C:8]([O:12][CH3:13])=[C:9]([O:10][CH3:11])[C:4]([O:3][CH3:2])=[CH:5][C:6]=4[O:21][C:20](=[O:22])[C:15]=3[CH2:16]1)[CH2:40]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 131369141,2,3,4-Tetrahydro-8,9,10-trimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochloride

Product 1

HCID 204881463-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8,9,10-trimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochlorideYield 37%

Procedure

Prepared by the method described in Example 13 from 1,2,3,4-tetrahydro-8,9,10-trimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochloride (10.0 g, 0.031 moles), triethylamine (6.8 g, 0.067 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (7.5 g, 0.034 moles). The crude product began to precipitate as the monohydrochloride shortly after reflux of the reaction mixture began. The product is filtered and recrystallized several times from 2-methoxyethanol/water to yield the final product (5.5 g) as the monohydrochloride, mp 241°-243° C.

Workup

  1. customPrepared by the method
  2. customto precipitate as the monohydrochloride shortly
  3. temperatureafter reflux of the reaction mixture
  4. filtrationThe product is filtered
  5. customrecrystallized several times from 2-methoxyethanol/water

Sources & evidence

ORD record
ord-75d1d920cb8349eea9b96585e9aaf76f
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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