Tributyl phosphite → Dibutyl P-[1-(N-Octadecyl-N-butoxyamino)octadecyl]phosphonate

HRID 846842Notes

Reaction equation

[CH:1](=[N+:19]([O-:38])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[P:39]([O:50]CCCC)([O:45][CH2:46][CH2:47][CH2:48][CH3:49])[O:40][CH2:41][CH2:42][CH2:43][CH3:44].[CH2:55](I)[CH2:56][CH2:57][CH3:58]>>[CH2:1]([N:19]([CH:20]([P:39](=[O:50])([O:45][CH2:46][CH2:47][CH2:48][CH3:49])[O:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[O:38][CH2:55][CH2:56][CH2:57][CH3:58])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

Reactant 3

HCID 7623Tributyl phosphite

HCID 10962Butyl iodide

HCID 71340222N-Octadecyloctadecan-1-imine N-oxide

Product 1

HCID 19883783Dibutyl P-[1-(N-Octadecyl-N-butoxyamino)octadecyl]phosphonateYield 35%

Conditions

Temperature: 70 °C

Procedure

Following the procedure of Example 7, the title compound is prepared from 10.0 g (18 mmol) of N-(1-octadecylidene)octadecylamine N-oxide, 7.0 g (28 mmol) of tri-n-butyl phosphite and 5.15 g (28 mmol) of n-butyl iodide by heating at 70° C. for 16 hours. The residue is purified by flash chromatography (10:1 hexane:ethyl acetate eluent) followed by HPLC to give 4.9 g (35% yield) of the title compound as a white solid melting at 38°-40° C.

Workup

customThe residue is purified by flash chromatography (10:1 hexane:ethyl acetate eluent)

Sources & evidence

ORD record: ord-2cf4868f5eb34a1084ba0f6479a27a6a
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05137951

Reaction notes

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