Ammonia → HCID 20550383, compound

HRID 1704774Notes

Reaction equation

HRID 1704774 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH:6]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2.N.[Li].C(O)C>CCOCC.O>[CH3:20][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[C:19]2[CH2:18][CH:17]=[CH:16][CH2:15][C:14]=2[CH2:13][C:12]2[C:7]1=[CH:8][CH:9]=[CH:10][CH:11]=2

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 10333104HCID 10333104, compound

Product 1

HCID 20550383HCID 20550383, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 21.55 g of 9,10-dihydro-N,N-dimethyl-9-anthracenepropanamine in 100 ml of ether is added to 1 liter of liquid ammonia. Lithium ribbon (1.125 g) is added in several portions over a period of 5 minutes. After stirring for 15 minutes, absolute ethanol is added dropwise until the color is discharged (25 ml added in 30 minutes). More ether is added and the ammonia is boiled off. The mixture is then cooled in an ice bath and 500 ml of water is added. The layers are separated and the aqueous layer is reextracted with ether. The combined ether layers are dried over potassium carbonate, filtered, and the solvent is removed in vacuo leaving 21.2 g of crude product.

Workup

  1. addition(25 ml added in 30 minutes)
  2. temperatureThe mixture is then cooled in an ice bath
  3. customThe layers are separated
  4. dry with materialThe combined ether layers are dried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-f0c278f571fc40d3a0b1c68b30c74c0e
Source dataset
uspto-grants-1978_11
Patent number
US04127717

Reaction notes

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