Piperidine, 1-(3-chloropropyl)- → HCID 13671866, compound

HRID 1655324Notes

Reaction equation

HRID 1655324 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>C1C=CC=CC=1>[ClH:16].[ClH:16].[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

4

Reactant 2

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

Product 1

HCID 13671866HCID 13671866, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (1RS,2SR)-2-amino-5-methyl-1-phenylhexan-1-ol (1.04 g, 5 mmol) and 1-(3-chloropropyl)piperidine (0.81 g, 5 mmol) in benzene (10 ml) was refluxed for 40 hours. After being cooled, the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethanol (10 ml), followed by addition of 6N-HCl in EtOH (2 ml). Precipitated crystals were collected by filtration and then recrystallized from ethanol to obtain 1.15 g of the title compound as white crystals (yield: 57%).

Workup

  1. temperaturewas refluxed for 40 hours
  2. temperatureAfter being cooled
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethanol (10 ml)
  5. additionfollowed by addition of 6N-HCl in EtOH (2 ml)
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e7bcc7f90cd24802bd6f04e9fca54e56
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

Loading…