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

HRID 1995293Notes

Reaction equation

HRID 1995293 reaction equation
[Cl:1][C:2]1[C:3]([CH3:17])=[CH:4][C:5]2[O:15][C:14](=[O:16])[C:9]3[CH2:10][NH:11][CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1.C(N(CC)CC)C.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:35][CH:34]2[CH2:36][CH2:37][CH:31]([CH2:32][CH2:33]2)[CH2:30]1>>[CH:34]12[CH2:36][CH2:37][CH:31]([CH2:32][CH2:33]1)[CH2:30][N:29]([CH2:28][CH2:27][N:11]1[CH2:12][CH2:13][C:8]3[C:6]4[CH:7]=[C:2]([Cl:1])[C:3]([CH3:17])=[CH:4][C:5]=4[O:15][C:14](=[O:16])[C:9]=3[CH2:10]1)[CH2:35]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 13136928HCID 13136928, compound

Product 1

HCID 131890203-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-9-chloro-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 62.4%

Procedure

Prepared by the method described for Example 13 from 9-chloro-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one (2.0 g, 0.008 moles), 0.008 moles), triethylamine (2.3 ml, 0.017 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (1.8 g, 0.008 moles). Recrystallization from ethanol gave the product (2.0 g) as the hemihydrochloride, mp 255° C. (dec).

Workup

  1. customPrepared by the method
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-fa3404f9276f4abab9c96e6aedea0cb4
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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