6-Methoxy-1,2,3,4-tetrahydroisoquinoline → HCID 21462994, compound

HRID 1940564Notes

Reaction equation

HRID 1940564 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][CH2:6]2.CN([CH2:16][C:17]1[C:25]2[C:20](=[N:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH2:16][C:17]1[C:25]3[C:20](=[N:21][CH:22]=[CH:23][CH:24]=3)[NH:19][CH:18]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinolineHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 21462994HCID 21462994, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 6-methoxy-1,2,3,4-tetrahydroisoquinoline (prepared by the method of Helfer, Helv. Chim. Acta, 1924, 7, 945) (0.55 g, 3.36 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.59 g, 3.36 mmol) in toluene (3 ml) was heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from toluene afforded the title compound (0.31 g, 32%), m.p. 144°-146° C.; (Found: C, 73.04; H, 6.43; N, 14.10. C18H19N3O.0.1H2O requires C, 73.24; H, 6.55; N, 14.23%); δH (DMSO-d6) 2.67 (2H, br s, CH2), 2.76 (2H, t, J 5.4 Hz, CH2), 3.49 (2H, s, CH2), 3.69 (3H, s, OCH3), 3.78 (2H, s, CH2), 6.65 (2H, m, ArH), 6.89 (1H, d, 9 Hz, ArH), 7.01 (1H, dd, J 7.9, 4.7 Hz, 5-H), 7.40 (1H, d, J 2.2 Hz, ArH), 8.03 (1H, dd, J 7.7, 1.3 Hz, 4-H), 8.19 (1H, dd, J 4.6, 1.4 Hz, 6-H), and 11.47 (1H, br s, NH); m/z (CI+, NH3) 294 (M+1)+.

Workup

  1. customprepared by the method of Helfer, Helv
  2. temperatureat reflux under nitrogen for 18 h
  3. temperatureto cool
  4. customthe crystallised product collected
  5. customRecrystallisation from toluene

Sources & evidence

ORD record
ord-25e1726c2294456b8ae09bdce9e7fc5b
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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