N,N-Dimethyl-1,3-propanediamine → N1,N1-Dimethyl-N3-(4-nitrophenyl)-1,3-propanediamine

HRID 1110333Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][NH2:16].C(=O)([O-])[O-].[K+].[K+].C(N(CCOCCOC)CCOCCOC)COCCOC>>[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][NH:16][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamine

HCID 9590p-Fluoronitrobenzene

HCID 11430Potassium Carbonate

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-

Product 1

HCID 15868541N1,N1-Dimethyl-N3-(4-nitrophenyl)-1,3-propanediamineYield 85%

Procedure

To a stirred solution of 4-fluoronitrobenzene (7 g, 50 mmol), 3-dimethylaminopropylamine (6.1 g, 60 mmol) and potassium carbonate (7 g, 50 mmol) in 25 ml of dimethylsulfoixde was added 0.2 g of tris(3,6-dioxaheptyl)amine (TDA-1). The heterogenous mixture was heated at 90° for 2 h. After cooling to room temperature, 110 g of crushed ice was added to precipitate out the yellow product in 85% yield (9.5 g, 43 mmol).

Workup

temperatureThe heterogenous mixture was heated at 90° for 2 h
customto precipitate out the yellow product in 85% yield (9.5 g, 43 mmol)

Sources & evidence

ORD record: ord-3264b3c81cff432c900079ca0ea600f6
Source dataset: uspto-grants-1990_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04975092

Reaction notes

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