Ammonia → HCID 22758136, compound

HRID 442062Notes

Reaction equation

HRID 442062 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH:7]=1.CCOCC.N.[Li]>C(O)C>[CH3:15][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[C:14]2[CH2:13][CH:12]=[CH:11][CH2:10][C:9]=2[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 3283Diethyl EtherHCID 3028194LithiumHCID 22758131N,N-Dimethylinden-3-propylamine

Product 1

HCID 22758136HCID 22758136, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 35 g. (0.174 mole) of N,N-dimethylinden-3-propylamine in a total volume of 125 ml. of ether is added to 2 liters of liquid ammonia. Over 1 hr., 44 g. (6.3 g-atoms) of lithium ribbon is added at the reflux temperature. After a total of 3 hours, the reaction mixture is blue. 550 ml. of ethanol is added over 135 min. whereupon the blue color fades. The ammonia is allowed to evaporate overnight and the residue dissolved in 1500 ml. of water and extracted twice with ether. The ether extract gives 34.5 g. (98.6%) of crude diene upon drying and solvent removal which contains ca, 10% of the corresponding aromatic compound by nmr integration.

Workup

  1. customAfter a total of 3 hours
  2. customto evaporate overnight
  3. dissolutionthe residue dissolved in 1500 ml
  4. extractionof water and extracted twice with ether
  5. extractionThe ether extract
  6. customgives 34.5 g
  7. dry with material(98.6%) of crude diene upon drying
  8. customsolvent removal which

Sources & evidence

ORD record
ord-002dc9008c5b4e1c9279466359f67b61
Source dataset
uspto-grants-1977_08
Patent number
US04044040

Reaction notes

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