N,N-Diethyl-1,3-propanediamine → HCID 70382571, compound

HRID 1608296Notes

Reaction equation

HRID 1608296 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][N:10]([CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:24]([N:26]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:27][CH3:28])[CH3:25]>ClCCl>[OH2:21].[CH2:24]([N:26]([CH2:27][CH3:28])[CH2:29][CH2:30][CH2:31][NH:32][C:20](=[O:22])[CH2:19][CH2:18][N:10]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=[N:9]1)[CH3:25].[CH2:24]([N:26]([CH2:29][CH2:30][CH2:31][NH:32][C:20](=[O:22])[CH2:19][CH2:18][N:10]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:8]=[N:9]1)[CH2:27][CH3:28])[CH3:25]

Participants

4

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamine2×HCID 14723696Methyl 3-(4,5-diphenyl-1H-pyrazol-1-yl)propanoate

Product 1

HCID 70382571HCID 70382571, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.8 g (0.016 mol) of methyl 4,5-diphenyl-1H-pyrazole-1-propanoate of example 4 and 48 mL of diethylaminopropylamine was heated at 120°-125° C. under nitrogen for 14 hours. The excess diethylaminopropylamine was stripped in vacuo at 85° C. The residue was dissolved in dichloromethane, an unwanted solid residue was filtered off, and the methylene chloride solution was washed twice with water and once with brine. The product was extracted into chilled dilute hydrochloric acid, and the chilled aqueous acid was made basic with solid sodium bicarbonate and then sodium carbonate. The basic water was extracted 4 times with dichloromethane, the combined washings were dried over sodium sulfate, and stripped to yield 2.4 g viscous amber oil. The oily product was dried at 40° C. and 0.1 mm vacuum for 7 days to yield 1.6 g of the hemihydrate still as a viscous oil.

Workup

  1. customwas stripped in vacuo at 85° C
  2. filtrationan unwanted solid residue was filtered off
  3. washthe methylene chloride solution was washed twice with water and once with brine
  4. extractionThe product was extracted
  5. temperatureinto chilled dilute hydrochloric acid
  6. extractionThe basic water was extracted 4 times with dichloromethane
  7. dry with materialthe combined washings were dried over sodium sulfate

Sources & evidence

ORD record
ord-9fc13b8b33174ef894f08f360501bdc2
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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