Hydrochloric Acid → Dimyristylamine

HRID 397298

Reaction equation

HRID 397298 reaction equation
[CH2:1]([NH:15][C:16](=O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].B.C1COCC1.Cl.[OH-].[Na+]>>[CH2:16]([NH:15][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 11743046N-tetradecyltetradecanamide

Product 1

HCID 87077DimyristylamineYield 108.1%

Conditions

Temperature
50 °C

Procedure

N-myristyl myristamide (0.90 g; 2.1 mmole) was treated with borane THF (5 mL of 1 M solution, 5.0 mmole) and reacted at reflux for 3 hrs. The reaction mixture was carefully neutralized with 3N HCl aqueous solution and stirred at 50° C. for 20 min., the back neutralized with 2N NaOH aqueous solution. The mixture was concentrated, then partitioned between CH2Cl2 and saturated NaHCO3 aqueous solution, dried and concentrated, affording 0.93 g of product. NMR (CDCl3): δ2.59 (t, 2H, J=7.2 Hz), 1.40-1.55 (m, 2H), 1.15-1.40 (m, 22H), 0.88 (t, 3H, J=6.8 Hz).

Workup

  1. customreacted
  2. temperatureat reflux for 3 hrs
  3. concentrationThe mixture was concentrated
  4. custompartitioned between CH2Cl2 and saturated NaHCO3 aqueous solution
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b784db5513bb4b91a09a941cc80f1b90
Source dataset
uspto-grants-2003_08
Patent number
US06610664B2

Linked notes

Loading…