Toluene → 3-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amine

HRID 1385486Notes

Reaction equation

HRID 1385486 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][NH2:14])=[CH:7][N:6]=1.C1(C)C=CC=CC=1>O>[N:6]1[C:7]2[NH:14][CH2:13][CH2:12][CH2:11][C:8]=2[CH:9]=[CH:10][C:5]=1[CH2:4][CH2:3][CH2:2][NH2:1]

Participants

4

Reactant 2

HCID 1140TolueneHCID 98130173-[5-(3-Aminopropyl)pyridin-2-yl]propylamine

Product 1

HCID 98775993-(5,6,7,8-Tetrahydro-1,8-naphthyridin-2-yl)propan-1-amineYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A 100 mL round-bottom flask equipped with a N2 inlet was charged with 1-3 (2.54 g, 13.1 mmol), toluene (65 mL), and freshly grounded NaNH2 (2.69 g, 65.5 mmol). The flask was evacuated and back filled with N2 and placed in a 90° C. oil bath. After 15 h, water (1.18 mL, 65.5 mmol) was added slowly without removing the flask from the oil bath. Caution: an exothermic reaction occurs upon addition of water. After the addition of water, the resulting mixture was filtered while hot, followed by 65 mL of hot toluene (90° C.). The mother liquor was concentrated to yield 2.37 g (94%) of 1-4.

Workup

  1. customA 100 mL round-bottom flask equipped with a N2 inlet
  2. customThe flask was evacuated
  3. additionback filled with N2
  4. customplaced in a 90° C.
  5. customwithout removing the flask from the oil bath
  6. customCaution: an exothermic reaction
  7. filtrationthe resulting mixture was filtered while hot,
  8. customfollowed by 65 mL of hot toluene (90° C.)
  9. concentrationThe mother liquor was concentrated

Sources & evidence

ORD record
ord-21dde4d1e303406b86abf0c6dade0e5f
Source dataset
uspto-grants-2001_07
Patent number
US06262268B1

Reaction notes

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