Water → HCID 23456460, compound

HRID 1973455Notes

Reaction equation

HRID 1973455 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][NH2:6])[CH3:3].[CH3:7][O:8][C:9]1[CH:24]=[CH:23][C:12]([C:13](=O)[CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C:16]2=O)=[CH:11][CH:10]=1.O>C(O)(=O)C>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][N:6]1[C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=2[CH:14]=[C:13]1[C:12]1[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 66053N,N-DimethylethylenediamineHCID 12270325Cyclohexanone, 2-[2-(4-methoxyphenyl)-2-oxoethyl]-

Product 1

HCID 23456460HCID 23456460, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4.41 g (0.05 mole) of dimethylaminoethylamine are added dropwise to a stirred suspension of 12.32 g (0.05 mole) of 2-(p-methoxyphenacyl)cyclohexanone in glacial acetic acid. After refluxing overnight, ice and water are added, and the cloudy mixture is washed with ether. The aqueous solution is basified with 10% sodium carbonate and extracted with ether. Removal of the ether after drying over sodium sulfate gives a light brown oil which solidifies on cooling. The resulting solid is recrystallized from methanol to give 1-(2-dimethylaminoethyl)-2(p-methoxyphenyl)-4,5,6,7-tetrahydroindole as white needles, m.p. 81°-82° C.

Workup

  1. temperatureAfter refluxing overnight
  2. washthe cloudy mixture is washed with ether
  3. extractionextracted with ether
  4. customRemoval of the ether
  5. dry with materialafter drying over sodium sulfate
  6. customgives a light brown oil which
  7. temperatureon cooling
  8. customThe resulting solid is recrystallized from methanol

Sources & evidence

ORD record
ord-c0b6daf65529462fbf78743ce5d00c09
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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