Hydrochloric Acid → HCID 13671866, compound

HRID 1655330Notes

Reaction equation

HRID 1655330 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[ClH:11].[OH:12][CH:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14](=O)[CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18].C([BH3-])#N.[Na+]>CO>[ClH:11].[ClH:11].[CH3:18][CH:17]([CH3:19])[CH2:16][CH2:15][CH:14]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH:13]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 19049Piperidine-1-propylamineHCID 5003444Sodium cyanoborohydrideHCID 19791689HCID 19791689, compound

Product 1

HCID 13671866HCID 13671866, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-(3-aminopropyl)piperidine (285 mg, 2 mmol) in methanol (6 ml) was added 0.1 ml of 6.8N-HCl in MeOH, 1-hydroxy-5-methyl-1-phenylhexan-2-one (413 mg, 2 mmol) and sodium cyanoborohydride (126 mg, 2 mmol). The reaction mixture was stirred for 19 hours at room temperature. The mixture was concentrated under reduced pressure and to the residue was added lN-HCl and ether. The aqueous layer was separated, basified with a 10% NaOH aqueous solution and then extracted three times with ether. The combined ethereal extract was washed twice with water, dried over anhydrous sodium sulfate and then evaporated under reduced pressure. The residue was dissolved in ethanol (12 ml). To the solution was added 0.70 ml of 6N-HCl in EtOH and the resulting mixture was allowed to stand. Precipitated crystals were collected by filtration to obtain 228 mg of the title compound (yield: 28%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and to the residue
  2. additionwas added lN-HCl and ether
  3. customThe aqueous layer was separated
  4. extractionextracted three times with ether
  5. extractionThe combined ethereal extract
  6. washwas washed twice with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customevaporated under reduced pressure
  9. dissolutionThe residue was dissolved in ethanol (12 ml)
  10. additionTo the solution was added 0.70 ml of 6N-HCl in EtOH
  11. customPrecipitated crystals
  12. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-e1674a21ccd64d0a88c126219b9bf3ba
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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