Diethyl Ether → HCID 13821866, compound

HRID 1788923Notes

Reaction equation

HRID 1788923 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[N:9]2[CH:10]=[CH:11][C:12]3[C:17]([C:8]2=[N:7][C:6]=1[CH3:18])=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH3:3].[S:19]([O:24]C)([O:22][CH3:23])(=[O:21])=[O:20].[CH2:26](OCC)C>O1CCCC1>[CH3:23][O:22][S:19]([O-:24])(=[O:21])=[O:20].[CH3:18][C:6]1[N:7]=[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]2[C:5]=1[CH2:4][N+:2]([CH3:26])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6497Dimethyl SulfateHCID 13821830HCID 13821830, compound

Product 1

HCID 13821866HCID 13821866, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-dimethylaminomethyl-2-methylimidazo[2,1-a]isoquinoline (7.7 g) in tetrahydrofuran (20 ml) was added dropwise to a solution of dimethyl sulfate (15 ml) in tetrahydrofuran (40 ml) with ice-cooling and stirring, and the mixture was stirred for 2 hours under the same conditions. To the reaction mixture was added diethyl ether (60 ml) and stirred with ice-cooling for 1 hour. The resulting precipitates were collected by filtration, washed with diethyl ether and recrystallized from ethanol to give 2-methyl-3-trimethylammoniomethylimidazo[2,1-a]isoquinoline methylsulfate (10 g).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 hours under the same conditions
  3. stirringstirred with ice-
  4. temperaturecooling for 1 hour
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed with diethyl ether
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-05a503c69e62474e8c0cab369e6ea2f1
Source dataset
uspto-grants-1987_08
Patent number
US04686227

Reaction notes

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