Dimethylamine → 3-(Dimethylamino)propyl hexadecanoate

HRID 1489545Notes

Reaction equation

HRID 1489545 reaction equation
C(OC[CH2:12][N:13](C)[CH3:14])(=O)CCCCCCC.[C:16]([O:33][CH2:34][CH2:35][CH2:36]Br)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].CNC.C(Cl)(Cl)Cl.CO>C(#N)C>[C:16]([O:33][CH2:34][CH2:35][CH2:36][N:13]([CH3:14])[CH3:12])(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 3075918Octanoic acid, 2-dimethylaminoethyl esterHCID 21584188Chloroform methanolHCID 22902160HCID 22902160, compound

Product 1

HCID 229021543-(Dimethylamino)propyl hexadecanoateYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This intermediate was prepared in a manner analogous to that of 2-(dimethylamino)ethyl octanoate from 3-bromopropyl hexadecanoate (3 g, 7.95 mmol) and 40% aqueous dimethylamine (15 mL, 119 mmol) in acetonitrile (20 mL). The resulting material was applied to a silica gel column (discontinuous gradient of chloroform/methanol 95:5, 8:2 as eluent) affording 1.3 g pure product. Yield 72%; mp 49°-50° C.; 1H NMR (CDCl3) 0.85-0.95 (t, CH3 (CH2)12), 1.20-1.40 (m, CH3 (CH2)12), 1.55-1.70 (m, CH2 CH2 CO), 1.88-2.00 (m, O CH2 CH2 CH2 N), 2.27-2.35 (t, CH2 CH2 CO), 2.37-2.45 (s, (CH3)2 N) 2.50-2.62 (t, O CH2 CH2 CH2 N), 4.10-4.18 (t, O CH2 CH2 CH2 N).

Sources & evidence

ORD record
ord-30e5fe1278d94b9397c258b33f155950
Source dataset
uspto-grants-1997_10
Patent number
US05679684

Reaction notes

Loading…