Water → (Dimethylaminoethyl)bis(1-cyclohexenyl)-methanol

HRID 1603180Notes

Reaction equation

HRID 1603180 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1.[Li].C(O[C:12](=[O:18])[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])C.O>C(OCC)C>[CH3:17][N:15]([CH2:14][CH2:13][C:12]([C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1)([C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1)[OH:18])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 135931-ChlorocyclohexeneHCID 88372beta-Alanine, N,N-dimethyl-, ethyl esterHCID 3028194Lithium

Product 1

HCID 54563448(Dimethylaminoethyl)bis(1-cyclohexenyl)-methanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-chloro-1-cyclohexene (5.8 g; 0.049 mol) was added to lithium (1.1 g; 0.049 mol) in diethyl ether (50 ml) in a single portion. After stirring overnight at room temperature, stirring was continued for 7 more hours with reflux. After cooling, ethyl-3-(N,N-dimethylamino)propionate (3.0 g; 0.021 mol) was added and as a result of the exothermic reaction refluxing occurred. After cooling to room temperature and stirring for another 30 minutes 100 ml of water was added. The water layer was separated off and extracted with diethyl ether. The combined ether layer was dried (K2CO3), filtered and evaporated. The yield was 4.5 g (83%).

Workup

  1. stirringstirring
  2. temperaturewith reflux
  3. temperatureAfter cooling
  4. customas a result of the exothermic reaction
  5. temperaturerefluxing
  6. temperatureAfter cooling to room temperature
  7. additionwas added
  8. customThe water layer was separated off
  9. extractionextracted with diethyl ether
  10. dry with materialThe combined ether layer was dried (K2CO3)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-ab7b9793bd624a9095e657265514e455
Source dataset
uspto-grants-1999_11
Patent number
US05986029

Reaction notes

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