Triethylamine → HCID 22048373, compound

HRID 1833113Notes

Reaction equation

HRID 1833113 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21]O)=[CH:9][N:8]=1.C(N(CC)CC)C.CS([Cl:37])(=O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH2:21][Cl:37])=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22048353HCID 22048353, compound

Product 1

HCID 22048373HCID 22048373, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

The above 1-(3-methoxybenzyl)-4-hydroxymethyl-6,7-dimethoxyisoquinoline (339 mg, 1.0 mmol) was dissolved in 5 ml of methylene chloride. Then at −30° C., triethylamine (160 ul, 1.10 eq) and methanesulfonyl chloride (85 ul, 1.10 eq) was added. The mixture was stirred at −30° C. for 30 minutes and then at room temperature overnight. The mixture was extracted with methylene chloride and water. After evaporation of solvents, a solid was obtained to give 1-(3-methoxybenzyl)-4-chloromethyl-6,7-dimethoxyisoquinoline (361 mg, 100%). ES-MS calculated for C20H20O3NCl (m/e) 357.39, observed 358.5 (M+1).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe mixture was extracted with methylene chloride and water
  4. customAfter evaporation of solvents
  5. customa solid was obtained

Sources & evidence

ORD record
ord-41126df92df34a8fb2edfdc6af9af7cd
Source dataset
uspto-grants-2006_06
Patent number
US07067529B2

Reaction notes

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