Triethylamine → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochloride

HRID 1995295Notes

Reaction equation

HRID 1995295 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[C:9]2[O:10][C:11](=[O:18])[C:12]3[CH2:13][NH:14][CH2:15][CH2:16][C:17]=3[C:8]=2[CH:7]=[CH:6][C:5]=1[O:19][CH3:20].C(N(CC)CC)C.Cl.[Cl:29][CH2:30][CH2:31][N:32]1[CH2:38][CH:37]2[CH2:39][CH2:40][CH:34]([CH2:35][CH2:36]2)[CH2:33]1>>[ClH:29].[ClH:1].[CH:37]12[CH2:39][CH2:40][CH:34]([CH2:35][CH2:36]1)[CH2:33][N:32]([CH2:31][CH2:30][N:14]1[CH2:15][CH2:16][C:17]3[C:8]4[CH:7]=[CH:6][C:5]([O:19][CH3:20])=[C:4]([O:3][CH3:2])[C:9]=4[O:10][C:11](=[O:18])[C:12]=3[CH2:13]1)[CH2:38]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 13136912HCID 13136912, compound

Product 1

HCID 204881493-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochlorideYield 8.8%

Procedure

Prepared by the method described in Example 9 from 1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one hydrochloride (6.0 g, 0.020 moles), triethylamine (4.0 g, 0.040 moles), and 3-(2-chloroethyl)-3-azabicyclo[3.2.2]nonane hydrochloride (5.4 g, 0.024 moles). Recrystallization from 95% ethanol and then from methanol yielded the product (0.85 g) as the dihydrochloride, mp 255°-258° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from 95% ethanol

Sources & evidence

ORD record
ord-26520752b71e464590e970e00319beec
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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