Water → HCID 14796677, compound

HRID 1493747Notes

Reaction equation

HRID 1493747 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]1C2[CH:11]=[CH:12][C:13](C=NC3CCCCC3)=[CH:14][C:9]=2[O:8][CH2:7]1.C(I)C.[OH2:26]>CCCCCC.C1COCC1>[CH2:3]([C:2]1[C:1]2[O:6][CH2:7][O:8][C:9]=2[CH:14]=[CH:13][C:12]=1[CH:11]=[O:26])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 465501658343-42-3HCID 178418339Butyllithium

Product 1

HCID 14796677HCID 14796677, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

n-Butyl lithium in hexane (1.6M, 320 ml) was added under nitrogen to a stirred solution of N-(1,3-benzodioxol-5-ylmethylene)cyclohexanamine (100 g) in dry THF (500 ml) at -78°. After 15 min ethyl iodide (50 ml) was added and the mixture was allowed to warm slowly to -50°. Water was then added and the mixture was extracted with ether. The extracts were concentrated in vacuo and the concentrate heated in 2N hydrochloric acid (250 ml) on a steam bath for 20 min. The resultant solution was diluted with water and extracted with ether. The extracts were dried and evaporated to give the title compound (38 g) as a pale yellow oil. T.l.c. (ether:hexane, 1:9) Rf 0.3.

Workup

  1. temperatureto warm slowly to -50°
  2. extractionthe mixture was extracted with ether
  3. concentrationThe extracts were concentrated in vacuo
  4. temperaturethe concentrate heated in 2N hydrochloric acid (250 ml) on a steam bath for 20 min
  5. additionThe resultant solution was diluted with water
  6. extractionextracted with ether
  7. customThe extracts were dried
  8. customevaporated

Sources & evidence

ORD record
ord-28b7f365de4d40a7929658b9614a5606
Source dataset
uspto-grants-1991_06
Patent number
US05023378

Reaction notes

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