2-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinoline → HCID 86729247, compound

HRID 1399920Notes

Reaction equation

HRID 1399920 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[C:8]([C:11]3[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=3)[NH2:14])[CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[O:18]1[CH2:20][CH:19]1[CH2:21][N:22]1[CH2:31][CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1>CCO>[CH2:23]1[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30][CH2:31][N:22]1[CH2:21][CH:19]([OH:18])[CH2:20][NH:14][C:13]1[CH:15]=[CH:16][CH:17]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:4]=[CH:3][N:2]([CH3:1])[C:6]=3[CH:7]=2)[CH:12]=1

Participants

4

Reactant 2

HCID 167845312-[(Oxiran-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolineHCID 867293063-(1-methyl-1H-benzo[d]imidazol-6-yl)aniline

Product 1

HCID 86729247HCID 86729247, compoundYield 29.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 3-(1-methyl-1H-benzo[d]imidazol-6-yl)aniline (300 mg, 1.34 mmol) in EtOH (3 mL) were added 2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (250 mg, 1.32 mmol). The reaction mixture was heated at 120° C. under microwave conditions for 30 min. After cooling, the resulting solution was concentrated in vacuuo and purified via column chromatography to yield the title compound (160 mg, 28.9%) LCMS (m/z): 413.2 [M+H]+

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting solution was concentrated in vacuuo
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-6305ef6468354c6cb971b7830858ac1f
Source dataset
uspto-grants-2014_12
Patent number
US08906900B2

Reaction notes

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