N,N,N',N'-Tetramethylmethanediamine → HCID 67336549, compound

HRID 1921215Notes

Reaction equation

HRID 1921215 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:12][N:13]([CH3:18])[CH2:14]N(C)C>CC(O)=O>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[C:4]([CH2:12][N:13]([CH3:18])[CH3:14])=[CH:5][NH:6]2

Participants

4

Reactant 2

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 98339914,6-dimethyl-1H-indole

Product 1

HCID 67336549HCID 67336549, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 4,6-dimethyl-1H-indole (Cho et al., Tetrahedron, 2001, 57, 3321-3330) (93.0 mg, 0.640 mmol) and N,N,N′,N′-tetramethylmethanediamine (98.0 mg, 0.961 mmol) in AcOH (3 mL) was stirred at ambient temperature for 2 h. The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (10 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (10 mL)
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74c70666a93e40c7a9de10a7da7e89f7
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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