1,2,3,4-Tetrahydroisoquinoline → HCID 11616091, compound

HRID 1894280Notes

Reaction equation

HRID 1894280 reaction equation
Cl[C:2]1[C:7]2[C:8]([CH3:12])=[C:9]([CH3:11])[NH:10][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][NH:14]1>>[CH3:11][C:9]1[NH:10][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:14]3[CH2:15][CH2:16][C:17]4[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH2:13]3)[C:7]=2[C:8]=1[CH3:12]

Participants

3

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 714120514-Chloro-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 11616091HCID 11616091, compoundYield 77.1%

Conditions

Temperature
160 °C

Procedure

A mixture of 4-chloro-2,3-dimethyl-1H-pyrrolo[3,2-c]pyridine (1.49 g, 8.25 mmol) prepared in Preparation 1 and 1,2,3,4-tetrahydroisoquinoline (4 ml) was stirred for 12 hours at 160° C. The reaction mixture was cooled to room temperature and purified with silica gel column chromatography (ethyl acetate) to give the titled compound as a white solid. (Yield: 77.1%)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompurified with silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-131c40bfd4e949baa702fc9917b29bea
Source dataset
uspto-grants-2013_08
Patent number
US08513277B2

Reaction notes

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