Triethylamine → 3-[2-(3-Azabicyclo[3.3.1]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 1995305Notes

Reaction equation

HRID 1995305 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1.C(N(CC)CC)C.Cl.Cl[CH2:27][CH2:28][N:29]1[CH2:36][CH:35]2[CH2:37][CH:31]([CH2:32][CH2:33][CH2:34]2)[CH2:30]1>>[CH:35]12[CH2:37][CH:31]([CH2:32][CH2:33][CH2:34]1)[CH2:30][N:29]([CH2:28][CH2:27][N:12]1[CH2:13][CH2:14][C:9]3[C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[O:16][C:15](=[O:17])[C:10]=3[CH2:11]1)[CH2:36]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-oneHCID 204881433-(2-Chloroethyl)-3-azabicyclo[3.3.1]nonane hydrochloride

Product 1

HCID 131890353-[2-(3-Azabicyclo[3.3.1]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 48.3%

Procedure

Prepared by the method described for Example 13 from 1,2,3,4-tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one (3.0 g, 0.013 moles), triethylamine (7.2 ml, 0.052 moles), and 3-(2-chloroethyl)-3-azabicyclo-[3.3.1]nonane hydrochloride (3.25 g, 0.015 moles). Recrystallization from ethanol gave the product (2.4 g), mp 102°-103° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-478b1e82b75e4d5dadc28725b650cea6
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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