3-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1) → 3-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-phenyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one, dihydrochloride

HRID 1995290Notes

Reaction equation

HRID 1995290 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]3[C:13]4[CH2:18][CH2:17][NH:16][CH2:15][C:14]=4[C:19](=[O:21])[O:20][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:22].[Cl:23][CH2:24][CH2:25][N:26]1[CH2:32][CH:31]2[CH2:33][CH2:34][CH:28]([CH2:29][CH2:30]2)[CH2:27]1>>[ClH:23].[ClH:22].[CH:31]12[CH2:33][CH2:34][CH:28]([CH2:29][CH2:30]1)[CH2:27][N:26]([CH2:25][CH2:24][N:16]1[CH2:17][CH2:18][C:13]3[C:10]4[CH:11]=[CH:12][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[CH:8][C:9]=4[O:20][C:19](=[O:21])[C:14]=3[CH2:15]1)[CH2:32]2

Participants

3

Reactant 2

HCID 126123263-(2-Chloroethyl)-3-azabicyclo[3.2.2]nonane--hydrogen chloride (1/1)HCID 131369208-Phenyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131890163-[2-(3-Azabicyclo[3.2.2]non-3-yl)ethyl]-1,2,3,4-tetrahydro-8-phenyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one, dihydrochlorideYield 9.2%

Procedure

Prepared by the method described for Example 1 from 8-phenyl-1,2,3,4-tetrahydro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (5.54 g, 0.02 moles) and 3-(2-chloroethyl)-3-azabicyclo(3.2.2)nonane hydrochloride (4.48 g, 0.02 moles). Recrystallization from methanol gave the product (920 mg), mp 260°-265° C. (dec).

Workup

  1. customPrepared by the method
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-bf2c665a26ac4c76a6ecf4ad6fd56e38
Source dataset
uspto-grants-1983_09
Patent number
US04404138

Reaction notes

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