Diisoamyl ketone → 1-[7-[4-Methyl-1-(3-methylbutyl)pentylamino]heptyl]piperidine

HRID 1033473Notes

Reaction equation

HRID 1033473 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][C:6](=O)[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH3:3].[NH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.C(O)C.[BH4-].[Na+]>CO>[CH3:1][CH:2]([CH3:3])[CH2:4][CH2:5][CH:6]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1)[CH2:7][CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 62421Diisoamyl ketoneHCID 4311764Sodium borohydrideHCID 117456341-PiperidineheptanamineHCID 21887872Ethanol hydrochloride

Product 1

HCID 150300441-[7-[4-Methyl-1-(3-methylbutyl)pentylamino]heptyl]piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.70 g of 2,8-dimethylnonan-5-one and 1.98 g of 1-(7-aminoheptyl)piperidine in 50 ml of methanol was added 6 N hydrochloric acid-ethanol to have a pH value of approx. 7 (pH test paper). To the resulting solution was added under cooling 1.26 g of sodium borohydride all at once. The resulting mixture was stirred under chilling with ice for one hour, and then stirred overnight at room temperature. The reaction mixture was concentrated, and the residue was extracted with chloroform after addition of water and an aqueous sodium hydroxide solution. The chloroform portion was dried and evaporated under reduced pressure to remove the solvent, yielding an oily product. The oily product was purified by silica gel column chromatography (eluent: chloroform-methanol 80:1 to 40:1) to give the desired compound as a colorless oil.

Workup

  1. additionTo the resulting solution was added
  2. temperatureunder chilling with ice for one hour
  3. stirringstirred overnight at room temperature
  4. concentrationThe reaction mixture was concentrated
  5. extractionthe residue was extracted with chloroform
  6. additionafter addition of water
  7. dry with materialThe chloroform portion was dried
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customyielding an oily product
  11. customThe oily product was purified by silica gel column chromatography (eluent: chloroform-methanol 80:1 to 40:1)

Sources & evidence

ORD record
ord-14d5b1583a364bb2ad3dca6faf791f97
Source dataset
uspto-grants-1994_05
Patent number
US05310902

Reaction notes

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