Ammonia → HCID 21521229, compound

HRID 918550Notes

Reaction equation

HRID 918550 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.N.[Li].C(O)C>CCOCC>[CH3:1][NH:2][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 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 215212273-(1H-Inden-1-yl)-N-methylpropan-1-amine

Product 1

HCID 21521229HCID 21521229, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 40 g of 1-[3-(methylamino)propyl]indene in 200 ml of absolute ether is added to 2.5 liters of liquid ammonia at -33°C. Lithium ribbon (35 g) is added over 1.5 hours. The bronze mixture is stirred for 1 hour, and treated with absolute ethanol over 2 hours until the blue color is discharged. The ammonia is evaporated overnight, whereupon water and ether are added with cooling in an ice bath. The layers are separated, the aqueous layer reextracted, and the organic layers are dried (potassium carbonate) and evaporated to give 40 g of 4,7-dihydro-1-[3-(methylamino)propyl]indan as an oil. The crude diene is taken up in 400 ml of toluene and treated with 24 g of phenoxypropylbromide in 100 ml of toluene. The mixture is refluxed for 18 hours, cooled, diluted with ether, and washed several times with water. The organic layers are then shaken with excess 10% hydrochloric acid. The bottom colorless aqueous phase of the 3-phase mixture is drawn off, the toluene-ether layer is decanted, and the isolated middle layer washed with distilled water. The oily hydrochloride is then shaken with excess 10% sodium hydroxide and ether and the organic phase is separated and dried (potassium carbonate). Evaporation gives 25 g of N-methyl-N-phenoxypropylaminopropyl-4,7-dihydroindan.

Workup

  1. customThe ammonia is evaporated overnight, whereupon water and ether
  2. additionare added
  3. temperaturewith cooling in an ice bath
  4. customThe layers are separated
  5. dry with materialthe organic layers are dried (potassium carbonate)
  6. customevaporated

Sources & evidence

ORD record
ord-2ef3846f9ce74043a2b235f5acd1be13
Source dataset
uspto-grants-1976_07
Patent number
US03971823

Reaction notes

Loading…