Hydrochloric Acid → HCID 53846711, compound

HRID 1076780Notes

Reaction equation

HRID 1076780 reaction equation
C1(C#CC2C=CC(CCl)=CC=2)C=CC=CC=1.N1CCCCC1.Cl.Cl.[C:25]1([C:31]#[C:32][C:33]2[CH:45]=[CH:44][C:36]([CH2:37][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:35][CH:34]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(O)(C)C.C(O)C>[C:25]1([C:31]#[C:32][C:33]2[CH:34]=[CH:35][C:36]([CH2:37][N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:44][CH:45]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8082PiperidineHCID 21417396HCID 21417396, compoundHCID 68129063HCID 68129063, compound

Product 1

HCID 53846711HCID 53846711, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

4-(Phenylethynyl)-benzyl chloride, 0.57 g. (2.5 mmole), is added to 5 ml. of piperidine and the mixture, from which a precipitate separates, is stirred for about 3 hours at room temperature. After evaporation of the bulk of the excess piperidine under reduced pressure, the residue is triturated with benzene and the insoluble piperidine hydrochloride removed by filtration. The benzene filtrate is washed with water and dried (MgSO4). Evaporation of the benzene under reduced pressure leaves 0.74 g. of the product as the residual oil. This oil is dissolved in isopropyl alcohol and treated with a slight excess of 7.2 N. hydrogen chloride in absolute ethanol. The white crystalline precipitate is collected after chilling the mixture and is recrystallized from isopropyl alcohol to give 0.662 g. of N-(4-phenylethynylbenzyl)-piperidine hydrochloride, m.p. 254°-256°C.

Workup

  1. addition(2.5 mmole), is added to 5 ml
  2. customAfter evaporation of the bulk of the excess piperidine under reduced pressure
  3. customthe residue is triturated with benzene
  4. customthe insoluble piperidine hydrochloride removed by filtration
  5. washThe benzene filtrate is washed with water
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the benzene under reduced pressure
  8. customleaves 0.74 g
  9. additiontreated with a slight excess of 7.2 N
  10. customThe white crystalline precipitate is collected
  11. temperatureafter chilling the mixture
  12. customis recrystallized from isopropyl alcohol
  13. customto give 0.662 g

Sources & evidence

ORD record
ord-172070b2185f436296b6ac87bde5f16a
Source dataset
uspto-grants-1976_05
Patent number
US03957871

Reaction notes

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