Thiourea → 6,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline

HRID 893319Notes

Reaction equation

HRID 893319 reaction equation
NC(N)=S.ClCC([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH3:22])=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O>C(O)C>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:21][CH3:22])[CH:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[NH:9][CH2:18][CH2:17]2

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 37891952-Chloro-1-(6,7-dimethoxy-1-phenyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone

Product 1

HCID 1511866,7-Dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of thiourea (45 mg), the product of step B and ethanol (8 mL) at reflux for 3 h. Remove the solvent in vacuo, dissolve the residue in chloroform and filter. Concentrate the filtrate to give 153 mg of the title compound. 1H NMR (CDCl3): δ7.4-7.18 (5H, m); 6.63 (1H, s); 6.24 (1H, s); 5.03 (1H, s); 3.85 (3H, s); 3.61 (3H, s); 3.28-2.65 (4H, m); 2.3 (1H, br. s).

Workup

  1. temperatureHeat
  2. customRemove the solvent in vacuo
  3. dissolutiondissolve the residue in chloroform
  4. filtrationfilter
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-3a30662fbbda421b8c213f4e21356254
Source dataset
uspto-grants-1992_06
Patent number
US05124337

Reaction notes

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