Piperidine → HCID 20216182, compound

HRID 236561Notes

Reaction equation

HRID 236561 reaction equation
[CH2:1]([C:3]([OH:21])([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12]Br)=[CH:6][CH:5]=1)[CH3:2].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH2:1]([C:3]([OH:21])([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 8082PiperidineHCID 20216188HCID 20216188, compound

Product 1

HCID 20216182HCID 20216182, compound

Procedure

17.6 g. of α-ethyl-α-(4-fluorophenyl)-4-(2-bromoethoxy)-benzylalcohol and 30 ml. of dry piperidine are refluxed with stirring for two hours. Piperidine is distilled off from the reaction mixture under reduced pressure, to the residue water is added, and it is extracted with ether. The ethereal phase is washed to neutral with water, dried over anhydrous potassium carbonate, and then ether is distilled off. Crystallization of the residue from n-hexane yields 14.9 g. of the named compound, melting at 72° to 73° C.

Workup

  1. distillationPiperidine is distilled off from the reaction mixture under reduced pressure, to the residue water
  2. additionis added
  3. extractionit is extracted with ether
  4. washThe ethereal phase is washed to neutral with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. distillationether is distilled off
  7. customCrystallization of the residue from n-hexane
  8. customyields 14.9 g

Sources & evidence

ORD record
ord-63b42e631db2474b8a10cd283ed19534
Source dataset
uspto-grants-1987_02
Patent number
US04645774

Reaction notes

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