Triethylamine → HCID 13189026, compound

HRID 1995296Notes

Reaction equation

HRID 1995296 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]2[C:11]3[CH2:16][CH2:15][NH:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18][C:5]=2[CH:4]=1.C(N(CC)CC)C.[ClH:27].[Cl:28][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>>[ClH:28].[ClH:27].[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:6]4[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=4[O:18][C:17](=[O:19])[C:12]=3[CH2:13]1)[CH2:37]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 108252898,9-dimethoxy-1,2,3,4-tetrahydro-5H-chromeno[3,4-c]pyridin-5-oneHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)

Product 1

HCID 13189026HCID 13189026, compoundYield 34%

Procedure

Prepared by the method described in Example 9 from 1,2,3,4-tetrahydro-8,9-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one (5.2 g, 0.020 moles), triethylamine (4.9 g, 0.048 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (5.4 g, 0.024 moles). Recrystallization from methanol yielded the final product (3.3 g) as the dihydrochloride, mp 229°-234° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-27c11fe6a39a4da6a9e5bf254850b670
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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