Triethylamine → N-(3,4-diaminophenyl)-2-(diethylamino)acetamide

HRID 1091639Notes

Reaction equation

HRID 1091639 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[NH2:11])([O-])=O.[Na+].[CH2:13]([N:15]([CH2:20][CH3:21])[CH2:16][C:17]([O-])=[O:18])[CH3:14].CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.C(N(CC)CC)C>C(#N)C.C(O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([NH:10][C:17](=[O:18])[CH2:16][N:15]([CH2:20][CH3:21])[CH2:13][CH3:14])[CH:7]=[CH:6][C:5]=1[NH2:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 43383702-Nitro-4-phenylenediamineHCID 23670834Glycine, N,N-diethyl-, sodium salt (1:1)

Product 1

HCID 66593690N-(3,4-diaminophenyl)-2-(diethylamino)acetamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

2-Nitrobenzene-1,4-diamine (1.55 g, 10.1 mmol), N,N-diethylglycine sodium salt (1.61 g, 10.6 mmol) and DEPBT (3.02 g, 10.0 mmol) were suspended in acetonitrile (75 mL). Triethylamine (2.8 mL, 20.0 mmol) was added and the solution stirred overnight at room temperature. The brown precipitate which was formed was filtered and discarded. The filtrate was concentrated and the residue partitioned between EA and saturated aqueous sodium bicarbonate. The organic phase was washed with water and then with brine, dried over sodium sulfate, and the solvent removed under reduced pressure. The residue was dissolved in ethanol (50 mL) and hydrogenated at atmospheric pressure with 10% palladium on charcoal (1.0 g, 0.9 mmol) at room temperature overnight. Filtration and concentration under reduced pressure gave N-(3,4-diaminophenyl)-2-(diethylamino)acetamide as a light brown semi-solid, which solidified and turned blue on standing.

Workup

  1. customThe brown precipitate which was formed
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated
  4. customthe residue partitioned between EA and saturated aqueous sodium bicarbonate
  5. washThe organic phase was washed with water
  6. dry with materialwith brine, dried over sodium sulfate
  7. customthe solvent removed under reduced pressure
  8. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-bd23b24b0e704bdcb05f4b922f251601
Source dataset
uspto-grants-2012_03
Patent number
US08129396B2

Reaction notes

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