2,2-Dimethyl-1,3-propanediamine → HCID 18353695, compound

HRID 430063

Reaction equation

HRID 430063 reaction equation
Cl[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH3:14][C:15]([CH3:20])([CH2:18][NH2:19])[CH2:16][NH2:17].C(N)(N)CC.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[NH3:3].[NH2:17][CH2:16][C:15]([CH3:20])([CH3:14])[CH2:18][NH:19][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

7

Reactant 4

HCID 817702,2-Dimethyl-1,3-propanediamineHCID 516892Sodium BicarbonateHCID 123691662-Chloro-4-methoxyquinolineHCID 149540721,​1-​Propanediamine

Product 2

HCID 222AmmoniaHCID 18353695HCID 18353695, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-4-methoxyquinoline (0.63 g, 3.25 mmol) and 2,2-dimethyl-1,3-propanediamine (2.00 g, 19.5 mmol) was stirred for 16 h at 75° C. in a sealed propanediamine (2.00 g, 19.5 mmol) was stirred for 16 h at 75° C. in a sealed NaHCO3 and ethyl acetate. The organic layer was dried (MgSO4) and concentrated onto silica, then chromatographed eluting with 5% then 10% methanol/CH2Cl2+0.5% 880 aqueous ammonia to give the title compound as a white solid (0.19 g, 23%). δH (CDCl3) 0.99 (6H, s, C(CH3)2), 2.57 (2H, s, 2′-H), 3.41 (2H, s, 4′-H), 3.96 (3H, s, OCH3), 5.98 (1H, s, 3-H), 7.12-7.93 (4H, m, ArH). MS (ES+) 260 (MH+).

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. concentrationconcentrated onto silica
  3. customchromatographed
  4. washeluting with 5%

Sources & evidence

ORD record
ord-b3e0f94bcec74bcd934eb12c62f59691
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Linked notes

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