Ammonium Chloride → HCID 22272787, compound

HRID 1064798Notes

Reaction equation

HRID 1064798 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15](=O)[CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:19][CH2:18]1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Cl-].[NH4+]>C1COCC1>[CH2:7]([NH:14][CH2:15][CH2:16][N:17]1[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][CH2:25][OH:26])[CH2:21][CH2:22]1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22272678HCID 22272678, compound

Product 1

HCID 22272787HCID 22272787, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (380 mg, 10 mmol) was added to a solution of this amide (1.50 g, 5.0 mmol) in THF (50 ml) with ice-cooling and stirring and the mixture was returned to room temperature and stirred for 15 minutes and then heated to reflux for 2 hours. Under ice-cooling and stirring, a saturated ammonium chloride solution was gradually added thereto until the reaction solution became turbid, the separated matters were filtered off through celite, the filtrate was dried over anhydrous sodium carbonate and the solvent was evaporated therefrom. The resulting residue was purified by a silica gel column chromatography (75 g of silica gel; developing solvent, ammonia-saturated methanol:chloroform=1:20) to provide 586 mg (yield 41%) of 3-[4-(2-heptylaminoethyl)piperazin-1-yl]propanol as colorless oil.

Workup

  1. temperaturecooling
  2. customwas returned to room temperature
  3. stirringstirred for 15 minutes
  4. temperatureheated
  5. temperatureto reflux for 2 hours
  6. temperatureUnder ice-cooling
  7. stirringstirring
  8. filtrationthe separated matters were filtered off through celite
  9. dry with materialthe filtrate was dried over anhydrous sodium carbonate
  10. customthe solvent was evaporated
  11. customThe resulting residue was purified by a silica gel column chromatography (75 g of silica gel; developing solvent, ammonia-saturated methanol:chloroform=1:20)

Sources & evidence

ORD record
ord-90fa2867c31b470c98639c8a607aa2a1
Source dataset
uspto-grants-2005_11
Patent number
US06969711B2

Reaction notes

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