4-Phenylpiperidine → HCID 21559963, compound

HRID 1578401Notes

Reaction equation

HRID 1578401 reaction equation
[C:1]([N:4]1[C:12]2[CH:11]=[C:10]3[O:13][CH2:14][O:15][C:9]3=[CH:8][C:7]=2[CH:6]([CH2:16][CH2:17]Br)[CH2:5]1)(=[O:3])[CH3:2].[C:19]1([CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[C:1]([N:4]1[C:12]2[CH:11]=[C:10]3[O:13][CH2:14][O:15][C:9]3=[CH:8][C:7]=2[CH:6]([CH2:16][CH2:17][N:28]2[CH2:29][CH2:30][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 698734-PhenylpiperidineHCID 21559973HCID 21559973, compound

Product 1

HCID 21559963HCID 21559963, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 580 mg. (18.6 mmol) of 5-acetyl-6,7-dihydro-7-(2-bromoethyl)-5H-1,3-dioxolo[4,5-f]indole and 600 mg. (37.2 mmol) of 4-phenylpiperidine in 30 ml. of toluene is heated at reflux temperature for 18 hours. The solvent is removed, and the residue is extracted with diethyl ether (2 × 25 ml.), and the solid is removed by filtration. The filtrate is evaporated to give a residue that crystallizes on trituration with petroleum ether. The material is recrystallized from dilute acetone to give crystals, m.p. 101°-103°C.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customThe solvent is removed
  3. extractionthe residue is extracted with diethyl ether (2 × 25 ml.)
  4. customthe solid is removed by filtration
  5. customThe filtrate is evaporated
  6. customto give a residue that
  7. customcrystallizes on trituration with petroleum ether
  8. customThe material is recrystallized from dilute acetone
  9. customto give crystals, m.p. 101°-103°C.

Sources & evidence

ORD record
ord-acc1677126d64b038ca75c9bdfa39261
Source dataset
uspto-grants-1976_02
Patent number
US03936464

Reaction notes

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