Ammonia → HCID 12393829, compound

HRID 427111Notes

Reaction equation

HRID 427111 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]2[OH:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N.[Li].C(O)C>CCOCC>[N:1]1([CH2:7][CH2:8][CH2:9][CH:10]2[C:18]3[CH2:17][CH:16]=[CH:15][CH2:14][C:13]=3[CH2:12][CH:11]2[OH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 702EthanolHCID 3028194LithiumHCID 12393827HCID 12393827, compound

Product 1

HCID 12393829HCID 12393829, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The crude 1-(3-piperidinopropyl)-2-indanol (~0.2 M) is dissolved in 300 ml ether and added to 2 liters liquid ammonia. Lithium ribbon (50 g) is added in small portions over a period of 30 minutes. After stirring 11/2 hours, absolute ethanol is added dropwise until the color is discharged (~1 liter added over a period of 4 hours). The ammonia is allowed to evaporate and the residue is then diluted to 4 liters with water; two ether extracts yield 62 g of crude diene which becomes partially crystalline on standing.

Workup

  1. additionis added dropwise until the color
  2. additionadded over a period of 4 hours)
  3. customto evaporate
  4. additionthe residue is then diluted to 4 liters with water

Sources & evidence

ORD record
ord-6b17f2c92faa4877ac8d2abfc6a00a4e
Source dataset
uspto-grants-1979_10
Patent number
US04172945

Reaction notes

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