Water → N,N-Dimethylinden-3-propylamine

HRID 1704657Notes

Reaction equation

HRID 1704657 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15]Cl.[OH-].[Na+].O>CO>[CH3:11][N:12]([CH3:17])[CH2:13][CH2:14][CH2:15][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7219IndeneHCID 14798Sodium HydroxideHCID 943083-(Dimethylamino)propyl chloride hydrochloride

Product 1

HCID 22758131N,N-Dimethylinden-3-propylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 232 g. (2.0 moles) of indene and the free base prepared from 264 g. (1.6 moles) of 3-dimethylaminopropylchloride-hydrochloride is added in portions over 1 hour to a rapidly stirred mixture of 300 g. (7.5 moles) of sodium hydroxide, 300 g. of water and 300 ml. of 40% Triton B in methanol. The initial temperature is 50° and the rate of addition controlled to keep the temperature between 55°-60°. The green mixture is stirred at 60° for 4 hours, cooled, diluted with 1500 ml. of water and extracted with ether. The ether extract is in turn extracted with a solution of 180 ml. of conc. hydrochloric acid in 600 ml. of water and the aqueous phase separated, basified with 100 g. of sodium hydroxide and extracted with ether. Solvent removal gives 182 g. of brown oil which is distilled to give 102 g. of oil, b.p. 88°-93° at 0.05 mm. Redistillation gives 19.6 g.; b.p. 87.5°-89.5° at 0.05 mm. and 71.1 g., b.p. 89.5°-90° at 0.05 mm.

Workup

  1. additionA mixture of 232 g
  2. customis 50°
  3. additionthe rate of addition
  4. custombetween 55°-60°
  5. temperaturecooled
  6. additiondiluted with 1500 ml
  7. extractionof water and extracted with ether
  8. extractionThe ether extract
  9. extractionextracted with a solution of 180 ml
  10. customof water and the aqueous phase separated
  11. extractionof sodium hydroxide and extracted with ether
  12. customSolvent removal
  13. customgives 182 g
  14. distillationof brown oil which is distilled
  15. customto give 102 g
  16. distillationRedistillation
  17. customgives 19.6 g

Sources & evidence

ORD record
ord-8298b05ae03a49388d4da96b26e04bb7
Source dataset
uspto-grants-1978_11
Patent number
US04127578

Reaction notes

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