1,3-Propanediamine → HCID 6425211, compound

HRID 430059Notes

Reaction equation

HRID 430059 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH2:15][CH2:16][CH2:17][CH2:18][NH2:19]>>[NH2:15][CH2:16][CH2:17][CH2:18][NH:19][C:2]1[CH:11]=[C:10]([O:12][CH2:13][CH3:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 4281,3-PropanediamineHCID 8174292-Chloro-4-ethoxyquinoline

Product 1

HCID 6425211HCID 6425211, compoundYield 77%

Conditions

Temperature
60 °C

Procedure

To 2-chloro-4-ethoxyquinoline (J. Chem. Soc. Perkin Trans. 1, 1993, 181; 323 mg, 1.56 mmol) was added 1,3-diaminopropane (3.9 ml, 47 mmol). The mixture was stirred under argon at 60° C. for 48 h. Excess diamine was removed in vacuo to leave a cream residue which was purified by flash chromatography on silica gel eluting with 6% (9:1 MeOH/NH3) in DCM to give the title compound as a white solid (294 mg, 77%): δH (CD3OD) 1.49 (3H, t), 1.79 (2H, m), 2.74 (2H, t), 3.51 (2H, t), 4.13 (2H, q), 6.09 (1H, s), 7.12 (1H, t), 7.45 (1H, t), 7.55 (1H, d), 7.90 (1H, d); MS (APCI−) 244 (100%, [M−H]−), 216 (34).

Workup

  1. customExcess diamine was removed in vacuo
  2. customto leave a cream residue which
  3. customwas purified by flash chromatography on silica gel eluting with 6% (9:1 MeOH/NH3) in DCM

Sources & evidence

ORD record
ord-802b9555487c4766855fc1c91ff8936b
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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