Water → HCID 12088101, compound

HRID 489786Notes

Reaction equation

HRID 489786 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([C:18]([NH2:20])=O)[CH2:14][CH2:13]1.O.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([CH2:18][NH2:20])[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22262580HCID 22262580, compound

Product 1

HCID 12088101HCID 12088101, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

To a suspension of lithium aluminum hydride (3.32 g, 70.0 mmol) in tetrahydrofuran (200 ml) was added dropwise a solution of 1-[3-(methyloxy)propyl]-4-piperidinecarboxamide (step 1, 7.00 g, 35.0 mmol) in tetrahydrofuran (50 ml) at 0° C. over 15 minutes. The mixture was stirred at 0° C. for 30 min and at 40° C. for 1.5 h. After cooling to 0° C., water (3.3 ml), 15% aqueous sodium hydroxide (3.3 ml) and water (10 ml) were carefully added dropwise. The resulting mixture was filtered through a pad of Celite and the filtrate was concentrated in vacuo to give 6.31 g (97%) of the title compound as a pale yellow oil.

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-99193f1c3f7444f7b90c678b6f9e5848
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

Loading…