2-Phenyl-1,3-dioxan-5-yl 4-(hexadecylamino)hydrocinnamate → 2-Hydroxy-1-(hydroxymethyl)ethyl 4-(hexadecylamino)hydrocinnamate

HRID 1702685Notes

Reaction equation

HRID 1702685 reaction equation
[CH2:1]([NH:17][C:18]1[CH:40]=[CH:39][C:21]([CH2:22][CH2:23][C:24]([O:26][CH:27]2[CH2:32][O:31]C(C3C=CC=CC=3)[O:29][CH2:28]2)=[O:25])=[CH:20][CH:19]=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][CH2:14][CH2:15][CH3:16].[H][H]>[Pd].C(O)(=O)C>[CH2:1]([NH:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:22][CH2:23][C:24]([O:26][CH:27]([CH2:28][OH:29])[CH2:32][OH:31])=[O:25])=[CH:39][CH:40]=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][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 536327232-Phenyl-1,3-dioxan-5-yl 4-(hexadecylamino)hydrocinnamateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 540874802-Hydroxy-1-(hydroxymethyl)ethyl 4-(hexadecylamino)hydrocinnamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-phenyl-1,3-dioxan-5-yl 4-(hexadecylamino)hydrocinnamate, 10% palladium-on-carbon and acetic acid is treated with hydrogen in a Parr apparatus at room temperature until hydrogen uptake ceases. The mixture is filtered and the filtrate is evaporated. Recrystallization of the residue from chloroform provides the title compound.

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. customRecrystallization of the residue from chloroform

Sources & evidence

ORD record
ord-725f4360b40c430493054031178b1f00
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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