Succinic anhydride → 1-Hexadecanamine, 3,7,11,15-tetramethyl-

HRID 2228418Notes

Reaction equation

HRID 2228418 reaction equation
[CH2:1]([NH2:21])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH2:7][C@@H:8]([CH2:10][CH2:11][CH2:12][C@@H:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])\[CH3:4].C1(=O)OC(=O)CC1>N1C=CC=CC=1>[CH2:1]([NH2:21])[CH2:2][CH:3]([CH2:5][CH2:6][CH2:7][CH:8]([CH2:10][CH2:11][CH2:12][CH:13]([CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH3:14])[CH3:9])[CH3:4]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 6476637HCID 6476637, compound

Product 1

HCID 108515701-Hexadecanamine, 3,7,11,15-tetramethyl-Yield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Phytylamine (2.32 g), succinic anhydride (1.16 g) and pyridine (10 ml) was stirred at room temperature for 48 hours. Most of the pyridine was removed under reduced pressure and the crude product dissolved in dichloromethane and washed with 2M HCl (2×100 ml). The organic was layer separated, dried (MgSO4) and concentrated in vacuo to dryness. The crude product was chromotographed (ethyl acetate as eluant) to give phytanamine hemisuccinamide 1.23 g (91%) as a thick liquid which solidified on standing 1H-n.m.r. (CDCl3) δ0.8-1.8 (m, 39H), 2.5 (m, 2H, CH2COO—), 2.6 (m, 2H, CH2COOH), 3.2 (m, 2H, CH2N—), 5.79 (b, 1H, NH), m/z (CI, CH4), 412 (M+)

Workup

  1. customMost of the pyridine was removed under reduced pressure
  2. dissolutionthe crude product dissolved in dichloromethane
  3. washwashed with 2M HCl (2×100 ml)
  4. customseparated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-8256ddd6e9db4bc6881a7bcd2b5612a5
Source dataset
uspto-grants-2002_07
Patent number
US06417009B1

Reaction notes

Loading…