Hydrogen Bromide → HCID 68144948, compound

HRID 1576667Notes

Reaction equation

HRID 1576667 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:17](Br)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Br.N1(O)CCCCC1>CC(C)=O>[CH2:17]([N:5]1[CH2:6][CH2:7][C:2]([OH:1])([C:8]2[CH:13]=[CH:12][C:11]3[O:14][CH2:15][O:16][C:10]=3[CH:9]=2)[CH2:3][CH2:4]1)[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 209351-HydroxypiperidineHCID 98116BromomethylstyreneHCID 150347154-(2H-1,3-Benzodioxol-5-yl)piperidin-4-ol

Product 1

HCID 68144948HCID 68144948, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.4 g. 4-hydroxy-4-(3.4-methylene dioxy phenyl) -piperidine are dissolved hot in 75 ml. acetone, the solution obtained is mixed with 2.5 g. cinnamyl bromide and the reaction mixture is heated at reflux to boiling over the course of 4 hours. After boiling for 1 hour, part of the hydrobromide of the piperidinol used as the starting compound forms a precipitate and this is filtered off on completion of the reaction. The filtrate is then evaporated to dryness and extracted 3 times with 70 ml. ether each time. The ether solutions are combined, concentrated and mixed with petroleum ether during which time 1-cinnamyl-4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine with a melting point of 114° - 115°C precipitates.

Workup

  1. additionis mixed with 2.5 g
  2. temperatureat reflux
  3. customto boiling over the course of 4 hours
  4. filtrationthis is filtered off on completion of the reaction
  5. customThe filtrate is then evaporated to dryness
  6. extractionextracted 3 times with 70 ml
  7. concentrationconcentrated
  8. additionmixed with petroleum ether during which time 1-cinnamyl-4-hydroxy-4-(3.4-methylene dioxy phenyl)-piperidine with a melting point of 114° - 115°C
  9. customprecipitates

Sources & evidence

ORD record
ord-f57d9905aa174052ad51d68cc7b89f75
Source dataset
uspto-grants-1976_09
Patent number
US03982001

Reaction notes

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