N,N-Dimethyl-1,3-propanediamine → HCID 15052357, compound

HRID 2165861Notes

Reaction equation

HRID 2165861 reaction equation
[CH3:1][C:2](=[N:4][NH:5][C:6]([NH2:8])=[O:7])[CH3:3].[CH3:9][N:10]([CH3:15])[CH2:11][CH2:12][CH2:13]N>>[C:2](=[N:4][NH:5][C:6]([NH:8][CH2:13][CH2:12][CH2:11][N:10]([CH3:15])[CH3:9])=[O:7])([CH3:3])[CH3:1]

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 669652-(1-Methylethylidene)hydrazinecarboxamide

Product 1

HCID 15052357HCID 15052357, compound

Procedure

Acetone semicarbazone (23 g) and 3-dimethylaminopropylamine (24.5 g) were heated to 175° C. over 40 minutes, then cooled and partitioned between t-butyl methyl ether and brine. The ether layer was concentrated to give 13.2 g waxy solid 2-isopropylidene-N-(3-dimethylaminopropyl)hydrazinecarboxamide (mp 49°-53° C.). Of this, 2.0 g was boiled 8 hr. in water maintained at a volume of 20 ml, then treated with 1.67 ml 12N HCl and concentrated in vacuo to give 2.5 g crude N-(3-dimethylaminopropyl)hydrazinecarboxamide dihydrochloride as a syrup. One fifth of the latter was reacted with 5-nitro-2-furaldehyde (0.282 g) in 6 ml 1:1 methanol-ethanol containing 0.16 ml pyridine at reflux for 30 minutes. The mixture was cooled and treated with 10 ml isopropanol to give 0.51 g of the title compound as a yellow solid, mp 200°-202° C. (dec.).

Workup

  1. temperaturecooled
  2. custompartitioned between t-butyl methyl ether and brine
  3. concentrationThe ether layer was concentrated

Sources & evidence

ORD record
ord-3d017d89e60b46b5b7719c68e1ea3cd9
Source dataset
uspto-grants-1990_07
Patent number
US04942170

Reaction notes

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