Water → HCID 21491579, compound

HRID 1973467Notes

Reaction equation

HRID 1973467 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7]([CH:16]1[CH2:20][CH2:19][CH2:18][C:17]1=O)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.O.[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25]>C(O)(=O)C.CCOCC>[C:23]([OH:28])(=[O:27])[C:24]([OH:26])=[O:25].[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][N:6]1[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:7][C:16]2[CH2:20][CH2:19][CH2:18][C:17]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 971Oxalic AcidHCID 80511N-Methyl-1,3-propanediamineHCID 10655725Cyclopentanone, 2-(2-oxo-2-phenylethyl)-

Product 1

HCID 21491579HCID 21491579, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

8.82 g (0.1 mole) of methylaminopropylamine are added to a solution of 20.35 g (0.1 mole) of 2-phenacylcyclopentanone in glacial acetic acid under nitrogen. After refluxing for 12 hours, water is added and the aqueous solution is washed with ether. The aqueous phase is basified with sodium carbonate and extracted with ether to give a reddish oil. The oil is dissolved in ether and is added to an ether solution of oxalic acid to give 1-(3-methylaminopropyl)-2-phenyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole oxalate, m.p. 184°-185° C.

Workup

  1. temperatureAfter refluxing for 12 hours
  2. washthe aqueous solution is washed with ether
  3. extractionextracted with ether
  4. customto give a reddish oil

Sources & evidence

ORD record
ord-4e4e697c1eef45d78e4efdd60526691f
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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