Triethylamine → 2-(3-Azabicyclo[3.3.1]non-3-yl)-9-chloro-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 1995308Notes

Reaction equation

HRID 1995308 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.ClCC[N:29]1[CH2:36][CH:35]2[CH2:37][CH:31]([CH2:32][CH2:33][CH2:34]2)[CH2:30]1>>[CH:31]12[CH2:37][CH:35]([CH2:34][CH2:33][CH2:32]1)[CH2:36][N:29]([CH:12]1[NH:11][CH2:10][C:9]3[C:14](=[O:16])[O:15][C:5]4[CH:4]=[C:3]([CH3:17])[C:2]([Cl:1])=[CH:7][C:6]=4[C:8]=3[CH2:13]1)[CH2:30]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13136928HCID 13136928, compoundHCID 204881433-(2-Chloroethyl)-3-azabicyclo[3.3.1]nonane hydrochloride

Product 1

HCID 867390212-(3-Azabicyclo[3.3.1]non-3-yl)-9-chloro-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-oneYield 64.4%

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 (1.2 g, 0.005 moles), triethylamine (1.4 ml, 0.010 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.3.1]nonane hydrochloride (1.1 g, 0.005 moles). Recrystallization from methanol gave the product (1.2 g), mp 147°-149° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-e6fe0794474f4dfbb827ffdb24612d9f
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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