Acetic Acid → HCID 21491543, compound

HRID 1973463Notes

Reaction equation

HRID 1973463 reaction equation
[CH2:1]([N:3]([CH2:6][CH2:7][NH2:8])[CH2:4][CH3:5])[CH3:2].[CH3:9][O:10][CH:11]1[CH2:16][CH2:15][C:14](=O)[CH:13]([CH2:18][C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=O)[CH2:12]1.[OH2:27].[C:28]([OH:31])(=[O:30])[CH3:29]>>[C:28]([OH:31])(=[O:30])[C:29]([OH:10])=[O:27].[CH2:1]([N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][N:8]1[C:14]2[CH2:15][CH2:16][CH:11]([O:10][CH3:9])[CH2:12][C:13]=2[CH:18]=[C:19]1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 60993N,N-DiethylethylenediamineHCID 21491546HCID 21491546, compound

Product 1

HCID 21491543HCID 21491543, compound

Procedure

5.8 g (0.05 mole) of diethylaminoethylamine are added dropwise to a stirred solution of 12.3 g (0.05 mole) of 4-methoxy-2-phenacylcyclohexanone in glacial acetic acid under nitrogen. After refluxing for 5 hours, ice and water are added and the aqueous solution is washed with ether. The ether solution is dried over sodium sulfate and concentrated to a brown oil. The oil is converted to the oxalate salt which is recrystallized from methanol to give 1-(2-diethylaminoethyl)-2-phenyl-5-methoxy-4,5,6,7-tetrahydroindole oxalate as tan crystals, dec. 172°-176° C.

Workup

  1. temperatureAfter refluxing for 5 hours
  2. washthe aqueous solution is washed with ether
  3. dry with materialThe ether solution is dried over sodium sulfate
  4. concentrationconcentrated to a brown oil
  5. customis recrystallized from methanol

Sources & evidence

ORD record
ord-d9c8c49c33654a368a855a4ddb879bc9
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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