Ammonia → HCID 20308041, compound

HRID 1287285Notes

Reaction equation

HRID 1287285 reaction equation
[CH2:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH:2]1[N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.CCOCC.N.[Li]>O1CCCC1.C(O)C>[CH2:1]1[CH:13]2[CH:5]([C:6]3[CH2:7][CH:8]=[CH:9][CH2:10][C:11]=3[CH2:12]2)[CH2:4][CH2:3][CH:2]1[N:14]1[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 3028194LithiumHCID 20308032HCID 20308032, compound

Product 1

HCID 20308041HCID 20308041, compoundYield 98.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.1 g (0.084 moles) of 1-(1,2,3,4-tetrahydrofluoren-2-yl)pyrrolidine, prepared as per Example 7, in 400 ml of tetrahydrofuran and 100 ml of ether is added to 2.5 l of liquid ammonia. 12.25 g (1.72 g-atoms) of lithium ribbon is added over 25 min and the mixture stirred for 15 minutes. 160 ml of ethanol is added over 2.5 hr., the ammonia evaporated and the residue added to 1 liter of cold water. The layers are separated and the aqueous layer is extracted with ether (2 × 300 ml). The combined ether layers are washed, dried and evaporated in vacuo to give 20.2 g of oil of the above title.

Workup

  1. custom, the ammonia evaporated
  2. additionthe residue added to 1 liter of cold water
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with ether (2 × 300 ml)
  5. washThe combined ether layers are washed
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a856183e22964c0a92910b478e8196bc
Source dataset
uspto-grants-1976_10
Patent number
US03984419

Reaction notes

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