6,7-Dimethoxy-1,2,3,4-Tetrahydroisoquinoline → 6,7-Dimethoxy-2-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline

HRID 1446322Notes

Reaction equation

HRID 1446322 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13](Cl)=[O:14])=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][NH:23][CH2:22][CH2:21]2>ClCCl>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[CH2:24][N:23]([C:13]([C:9]1[CH:10]=[N:11][O:12][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:14])[CH2:22][CH2:21]2

Participants

4

Reactant 2

HCID 156236,7-Dimethoxy-1,2,3,4-TetrahydroisoquinolineHCID 729429065-(P-tolyl)isoxazole-4-carbonyl chloride

Product 1

HCID 591700716,7-Dimethoxy-2-{[5-(4-methylphenyl)isoxazol-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-(4-methylphenyl)isoxazole-4-carbonyl chloride (10 mg, 0.045 mmol) in dichloromethane (1 mL) was added 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (11 mg, 0.052 mmol, 1.2 eq.), and the reaction mixture was stirred for 1 h. The solvent was removed, and the residue was purified by preparative reverse-phase HPLC to give the title compound. HRMS (ESI, pos. ion) m/z calcd for C22H22N2O4: 378.1580, found 378.1585.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-bef43a353b2540908f1cd70e2dda55ec
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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