Triethylamine → 3,4-Dihydro-N-2-pyridinyl-2-(1H)-isoquinolinamine

HRID 612449Notes

Reaction equation

HRID 612449 reaction equation
C(N(CC)CC)C.Br[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17]Br.[NH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[NH2:20]>CN(C)C=O.O.C(OCC)(=O)C>[N:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[NH:19][N:20]1[CH2:17][CH2:16][C:11]2[C:10](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 786452-HydrazinopyridineHCID 816791Alpha-bromo-2-(2-bromoethyl)toluene

Product 1

HCID 195952143,4-Dihydro-N-2-pyridinyl-2-(1H)-isoquinolinamineYield 65.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (10.0 ml) was added to a solution of 1-bromomethyl-2-(2-bromoethyl)benzene (10 g) and 2-hydrazinopyridine (3.9 g) in dimethylformamide (250 ml), and the mixture was stirred, under nitrogen, at ambient temperature for about 20 mins. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with ethyl acetate to afford 5.3 g (65%) of product. Recrystallization of the product from ethyl acetate gave the analytical sample, mp 116-117° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-5ac8838528ac4fefad4e4e667a3eca74
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

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