2-(2-Benzoyloxypropan-1-yl)-3-octadecylcarbamoyloxypropylamine → 2-Cyanomethyl-3-hexadecyloxypropylamine

HRID 728498Notes

Reaction equation

HRID 728498 reaction equation
[N:1]([CH2:4][CH:5]([CH2:24][C:25]#[N:26])[CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[N+]=[N-].C(OC(C)CC(COC(=O)NCCCCCCCCCCCCCCCCCC)CN)(=O)C1C=CC=CC=1>[Pd].CO>[C:25]([CH2:24][CH:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:4][NH2:1])#[N:26]

Participants

5

Reactant 2

HCID 148350122-(2-Benzoyloxypropan-1-yl)-3-octadecylcarbamoyloxypropylamineHCID 198842081-Azido-2-cyanomethyl-3-hexadecyloxypropane

Product 1

HCID 148350132-Cyanomethyl-3-hexadecyloxypropylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3.00 g (23 mM) of 1-azido-2-cyanomethyl-3-hexadecyloxypropane Vn1b and 300 mg of 10% palladium on charcoal in 100 ml of methanol is hydrogenated as described in (129) and the crude product of the titled compound IVn1 is obtained.

Sources & evidence

ORD record
ord-4e95e3dda10348eb9d39d4c7465da13e
Source dataset
uspto-grants-1991_09
Patent number
US05047540

Reaction notes

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