Ammonia → HCID 12805659, compound

HRID 1704773Notes

Reaction equation

HRID 1704773 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH2:5][C:6]1(O)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2.N.[Li]>CCOCC.O>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[C:12]2[CH2:13][CH:14]=[CH:15][CH2:16][C:11]=2[CH2:10][CH2:9][C:8]2[CH:17]=[CH:18][CH:19]=[CH:20][C:7]1=2

Participants

6

Reactant 3

HCID 222Ammonia2×HCID 14390AmitriptynolHCID 3028194Lithium

Product 1

HCID 12805659HCID 12805659, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol (50.2 g) is partially dissolved in 350 ml of ether and added to 2 liters of liquid ammonia. Lithium ribbon (4.73 g) is then added portionwise over a period of 15 minutes. After stirring for 20 minutes, absolute alcohol is added dropwise until the color is discharged (about 90 ml added over a period of 1 hour). More ether is added and the ammonia is boiled off. While cooling in an ice bath the mixture is diluted slowly with 1 liter of water. The layers are separated and the aqueous layer is reextracted with ether. The combined organic layers are dried over potassium carbonate, filtered, and the solvent is removed in vacuo, leaving 47.0 g of an oil. NMR indicates this is about 50% of the desired diene (the bulk of remaining material being unreduced starting material).

Workup

  1. additionadded over a period of 1 hour)
  2. temperatureWhile cooling in an ice bath the mixture
  3. customThe layers are separated
  4. dry with materialThe combined organic layers are dried over potassium carbonate
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-7db99d30d7384d80b52fe5b0eb0b2b52
Source dataset
uspto-grants-1978_11
Patent number
US04127717

Reaction notes

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