N,N-Diethyl-1,3-propanediamine → HCID 14699597, compound

HRID 704836Notes

Reaction equation

HRID 704836 reaction equation
C([C:3]1[N:7]([CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])[N:6]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.[CH2:25]([N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30]N)[CH3:26]>O>[CH2:25]([N:27]([CH2:32][CH3:33])[CH2:28][CH2:29][CH2:30][NH:11][C:9](=[O:10])[CH:8]([CH3:12])[N:7]1[CH:3]=[C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:6]1)[CH3:26]

Participants

4

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 86743852HCID 86743852, compound

Product 1

HCID 14699597HCID 14699597, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 27.3 g (0.085 mol) of ethyl 3,4-diphenyl-α-methyl-1H-pyrazole-1-acetamide of example 9 and 120 mL of 3-(diethylamino)propanamine was heated 5 hr on a steambath. The reaction was poured into water and extracted into ethyl acetate. The ethyl acetate layer was dried and stripped to an oil in which a solid slowly crystallized. The crystals were removed and recrystallized from cyclohexane to yield 6.2 g of N-[3-(diethylamino)propyl]-3,4-diphenyl-α-methyl-1H-pyrazole-1-acetamide, mp 87°-89° C.

Workup

  1. temperaturewas heated 5 hr on a steambath
  2. extractionextracted into ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. customslowly crystallized
  5. customThe crystals were removed
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-46b7246a2c184619930c773859b51285
Source dataset
uspto-grants-1991_01
Patent number
US04988725

Reaction notes

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