Methanol → HCID 59355185, compound

HRID 1023494Notes

Reaction equation

HRID 1023494 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][NH:5][CH2:6][C:7]([CH3:10])([NH2:9])[CH3:8].C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.CO>C(Cl)Cl>[CH3:11][N:2]([CH3:1])[CH2:3][CH2:4][N:5]1[CH2:6][C:7]([CH3:8])([CH3:10])[NH:9][C:17]1=[O:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 682631,1'-CarbonyldiimidazoleHCID 59355176HCID 59355176, compound

Product 1

HCID 59355185HCID 59355185, compoundYield 2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1-(2-(dimethylamino)ethyl)-2-methylpropane-1,2-diamine (23.2 mmol) in CH2Cl2 (50 ml) was added CDI (4.51 g, 27.8 mmol). The solution was stirred for 20 h, concentrated in vacuo, the resulting residue suspended in 800 ml diethyl ether, washed with 3× 200 ml 1M Na2CO3, 200 ml sat. NaCl, dried on MgSO4, and concentrated in vacuo. Flash chromatography (2.5%→20% MeOH:CH2Cl2) afforded the title compound as a clear oil (79.3 mg, 0.428 mmol, 2%) as well as additional material heavily contaminated with imidazole g). 1H NMR (CDCl3, 400 MHz) δ 1.24 (s, 6H), 2.23 (s, 6H), 2.41 (m, 2H), 3.24 (s, 2H), 3.34 (m, 2H), 4.96 (s, 1H). ESI/APCI (pos) expected for C9H19N3O: 185.15. Found: 186 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with 3× 200 ml 1M Na2CO3, 200 ml sat. NaCl
  3. customdried on MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad9a73bc5f214367965ceee3a50ae5c8
Source dataset
uspto-grants-2014_05
Patent number
US08722715B2

Reaction notes

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