N,N-Diethyl-1,3-propanediamine → HCID 136067515, compound

HRID 1608299Notes

Reaction equation

HRID 1608299 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([O:16]CC)=O)[N:11]=[CH:10][C:9]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:4][CH:3]=1.[CH2:25]([N:27]([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:28][CH3:29])[CH3:26]>>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:30][CH2:31][CH2:32][NH:33][C:14](=[O:16])[CH2:13][N:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=2)=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:10]=[N:11]1)[CH3:26]

Participants

3

Reactant 2

HCID 61011N,N-Diethyl-1,3-propanediamineHCID 135603711HCID 135603711, compound

Product 1

HCID 136067515HCID 136067515, compound

Procedure

A solution of 10 g (0.031 mol) of ethyl-5-(4-hydroxyphenyl)-4-phenyl-1H-pyrazole-1-acetate of example 6 in 48 mL of diethylaminopropylamine was stirred on a steam bath under nitrogen for 14 hours. The excess amine was removed in vacuo at 80° C., the residue dissolved in ethyl acetate, washed twice with water, once with brine and dried over sodium sulfate. The ethyl acetate was stripped to yield 12 g of a dark oil which was triturated in hot cyclohexane several times. The insoluble residue was combined with a small amount of a mixture of oil and crystals, which had separated from the cyclohexane on cooling, and recrystallized from ethyl acetate to yield 6.6 g of product, mp 110-113.

Workup

  1. customThe excess amine was removed in vacuo at 80° C.
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed twice with water, once with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-d91fa8931b344f7d87dbc36d7938dd3e
Source dataset
uspto-grants-1989_09
Patent number
US04870095

Reaction notes

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