Ammonia → HCID 70608468, compound

HRID 263225Notes

Reaction equation

HRID 263225 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@@H:10]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C@H:11]2[OH:20])[CH2:4][CH2:3]1.N.[Li].C(O)C>CCOCC.O>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C@@H:10]2[CH2:19][C:18]3[CH2:17][CH:16]=[CH:15][CH2:14][C:13]=3[CH2:12][C@H:11]2[OH:20])[CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 70608181HCID 70608181, compound

Product 1

HCID 70608468HCID 70608468, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 25.4 g (92.7 mmol) of the amine of Example 1 in 100 ml ether is added to 1 liter liquid ammonia. Lithium (10.0 g) is added portionwise over a period of 10 minutes. After stirring 30 minutes, absolute ethanol is added dropwise until the color is discharged (140 ml added in 1 hour). More ether is added and the ammonia is boiled off. While cooling in an ice bath, the mixture is diluted with 1 liter water. The layers are separated and the aqueous is reextracted with ether. The combined organic layers are dried over K2CO3, filtered, and the solvent is removed in vacuo leaving 27 g of the title compound in the form of an oil.

Workup

  1. addition(140 ml added in 1 hour)
  2. temperatureWhile cooling in an ice bath
  3. customThe layers are separated
  4. dry with materialThe combined organic layers are dried over K2CO3
  5. filtrationfiltered
  6. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-c0807510322542d78878ad43621c1dd6
Source dataset
uspto-grants-1979_05
Patent number
US04156723

Reaction notes

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