1,3-Propanediamine → HCID 14699575, compound

HRID 1608294Notes

Reaction equation

HRID 1608294 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][N:9](CC(OCC)=O)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:24][CH2:25][CH2:26][CH2:27][NH2:28].[CH2:29]([OH:31])[CH3:30]>>[NH2:24][CH2:25][CH2:26][CH2:27][NH:28][C:29](=[O:31])[CH2:30][N:8]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:10]=[N:9]1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 702EthanolHCID 14699552HCID 14699552, compound

Product 1

HCID 14699575HCID 14699575, compound

Procedure

A mixture of 7.96 g (0.026 mol) of ethyl 3,4-diphenyl-1H-pyrazole-1-acetate and 19.2 g (0.26 mol) of 1,3-diaminopropane in 13 mL of ethanol was stirred at 84°-87° C. for 3 hours and the solvent removed in vacuo. The resulting solid was chromatographed on 34 g of silica gel eluting with 1% isopropylamine in chloroform and a gradient from 0-30% methanol. The impurities came off at 2-4% methanol followed by 6.95 g of pure product. It was crystallized three times from isopropyl acetate to yield 6.09 g of N-(3-aminopropyl)-4,5-diphenyl-1H-pyrazole-1-acetamide (1:4) hydrate, mp 119°-120° C.

Workup

  1. customthe solvent removed in vacuo
  2. customThe resulting solid was chromatographed on 34 g of silica gel eluting with 1% isopropylamine in chloroform
  3. customIt was crystallized three times from isopropyl acetate

Sources & evidence

ORD record
ord-c1ea961a21cd42bb9e2ee811f5442653
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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