Ammonia → HCID 70607769, compound

HRID 263228Notes

Reaction equation

HRID 263228 reaction equation
[CH2:1]([N:3]([CH2:17]C)[CH2:4][CH2:5][C@@H:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][C@H:7]1[OH:16])C.N.CCO>CCOCC>[CH3:17][N:3]([CH3:1])[CH2:4][CH2:5][C@@H:6]1[CH2:15][C:14]2[CH2:13][CH:12]=[CH:11][CH2:10][C:9]=2[CH2:8][C@H:7]1[OH:16]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 702EthanolHCID 70607911HCID 70607911, compound

Product 1

HCID 70607769HCID 70607769, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 14.6 g (66.6 mmol) of trans-3-[2-(diethylamino)ethyl]-1,2,3,4-tetrahydro-2-naphthalenol (prepared as in Example 10) in 125 ml of ether is added to 1 liter of NH3 (liquid). To this stirred solution is added 10 l g of Li in pieces over 10 minutes. When the addition is complete, the reaction mixture is stirred for 30 minutes, after which time absolute EtOH (~ 150 ml) is added dropwise until the blue color is discharged. The NH3 is then allowed to evaporate, the residue is diluted with water, and this thoroughly extracted with ether. The combined ether extracts are washed with saturated aqueous NaCl, dried, and concentrated in vacuo to 13.4 g (92%) of the title compound as an oil.

Workup

  1. additionTo this stirred solution is added 10 l
  2. additionWhen the addition
  3. customto evaporate
  4. additionthe residue is diluted with water
  5. extractionthis thoroughly extracted with ether
  6. washThe combined ether extracts are washed with saturated aqueous NaCl
  7. customdried
  8. concentrationconcentrated in vacuo to 13.4 g (92%) of the title compound as an oil

Sources & evidence

ORD record
ord-b97966d0198143449ecb870f45fd3146
Source dataset
uspto-grants-1979_05
Patent number
US04156723

Reaction notes

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