Hydrochloric Acid → HCID 13671866, compound

HRID 1655321Notes

Reaction equation

HRID 1655321 reaction equation
[NH2:1][CH:2]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[Cl:16][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[ClH:26]>C(O)C>[ClH:16].[ClH:26].[CH3:14][CH:13]([CH3:15])[CH2:12][CH2:11][CH:2]([NH:1][CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 13671865HCID 13671865, compound

Product 1

HCID 13671866HCID 13671866, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (1RS,2RS)-2-amino-5-methyl-1- phenylhexan-1-ol (1.04 g, 5 mmol) and 1-(3-chloropropyl)piperidine (0.81 g, 5 mmol) was melted at 70° C. in a nitrogen atmosphere. The mixture was then heated at 110° to 120° C. for 3 hours. After being cooled, the reaction mixture was dissolved with heating in ethanol, followed by addition of concentrated hydrochloric acid (0.5 ml). The resulting mixture was concentrated and the residue was crystallized by treatment with ethanol and hexane. The crystals were collected by filtration, washed with ethanol-hexane and then recrystallized from ethanol-hexane to obtain 1.24 g of the title compound as white crystals (yield: 61%).

Workup

  1. temperatureThe mixture was then heated at 110° to 120° C. for 3 hours
  2. temperatureAfter being cooled
  3. dissolutionthe reaction mixture was dissolved
  4. concentrationThe resulting mixture was concentrated
  5. customthe residue was crystallized by treatment with ethanol and hexane
  6. filtrationThe crystals were collected by filtration
  7. washwashed with ethanol-hexane
  8. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-775a46e8a2e34001a59e6d736a7686b3
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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