Water → HCID 86642707, compound

HRID 2061101Notes

Reaction equation

HRID 2061101 reaction equation
[N:1]([C:4]([CH3:23])([CH3:22])[CH2:5][C:6]([N:8]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH3:9])=O)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:10]([N:8]([CH3:9])[CH2:6][CH2:5][C:4]([CH3:23])([NH2:1])[CH3:22])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 86642706HCID 86642706, compound

Product 1

HCID 86642707HCID 86642707, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

3-Azido-N-dodecyl-N,3-dimethylbutanamide (7.28 g, 22.4 mmol) was dissolved into anhydrous THF (50 mL) and added dropwise to a suspension of LAH (1.70 g, 2.0 equiv, 44.8 mmol) in anhydrous THF (100 mL) to maintain the reaction at reflux (30 min). After complete addition, the flask was fitted with a condenser and the reaction heated in a 70° C. oil bath for 8 h. The reaction mixture was cooled in an ice bath and water (1.7 mL) was added dropwise over 20 min. Then 15% NaOH solution (1.7 mL) was added dropwise over 10 min. The suspension was stirred for a further 10 min and water (1.7 mL) was added in one portion and the mixture stirred for 30 min to a give fine white suspension. The suspension was filtered through a pad of Celite® and washed with diethyl ether (2×100 mL). The combined filtrate was concentrated with a bath temperature between 10-13° C. to an orange liquid (5.61 g, 88.0%). LRMS (ESI+) for C18H40N2 (284.3); Found: 285 (MH+).

Workup

  1. temperatureto maintain
  2. customthe reaction
  3. temperatureat reflux (30 min)
  4. additionAfter complete addition
  5. customthe flask was fitted with a condenser
  6. temperatureThe reaction mixture was cooled in an ice bath
  7. stirringthe mixture stirred for 30 min to a give fine white suspension
  8. filtrationThe suspension was filtered through a pad of Celite®
  9. washwashed with diethyl ether (2×100 mL)
  10. concentrationThe combined filtrate was concentrated with a bath temperature between 10-13° C. to an orange liquid (5.61 g, 88.0%)

Sources & evidence

ORD record
ord-62effa12c07649389548917437fe3060
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

Loading…