Ammonia → HCID 20308023, compound

HRID 1763855Notes

Reaction equation

HRID 1763855 reaction equation
[N:1]1([CH2:7][CH:8]2[C:20]3[CH2:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=3[CH2:11][CH2:10][CH:9]2[CH2:21][OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N.[Li].C(O)C>CCOCC>[N:1]1([CH2:7][CH:8]2[CH:20]3[CH:12]([C:13]4[CH2:14][CH:15]=[CH:16][CH2:17][C:18]=4[CH2:19]3)[CH2:11][CH2:10][CH:9]2[CH2:21][OH:22])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 3028194LithiumHCID 20308034HCID 20308034, compound

Product 1

HCID 20308023HCID 20308023, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 16.3 g of crude 1,2,3,4-tetrahydro-1-(piperidinomethyl)fluorene-2-methanol, in the form of the free base, dissolved in 300 ml of ether is added to 1.5 liter of liquid ammonia. An amount of 8.4 g (1.2 moles) of lithium ribbon is added over 1.5 hr. and then 150 ml of abs. ethanol added over 60 minutes; the ammonia is evaporated and the residue cooled and partitioned between 400 ml of water and 300 ml of ether. The aqueous layer is washed with 2 × 250 ml of ether, and then the extracts are combined, washed with sat. sodium chloride solution, dried, and evaporated in vacuo to give 13.1 g (0.0434 moles) of the above titled compound.

Workup

  1. customthe ammonia is evaporated
  2. temperaturethe residue cooled
  3. custompartitioned between 400 ml of water and 300 ml of ether
  4. washThe aqueous layer is washed with 2 × 250 ml of ether
  5. washwashed with sat. sodium chloride solution
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-fee8a3271079428b88e68853c9bb43bb
Source dataset
uspto-grants-1978_09
Patent number
US04113726

Reaction notes

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