N-cyclopropyl-3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzamide → N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

HRID 337638

Reaction equation

HRID 337638 reaction equation
[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[C:10](/[CH:12]=[CH:13]/[CH2:14][O:15][CH3:16])[CH:9]=[C:8](/[CH:17]=[CH:18]/[CH2:19][O:20][CH3:21])[CH:7]=2)[CH2:3][CH2:2]1.[H][H]>[Pd].CCOC(C)=O>[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:7]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67061991N-cyclopropyl-3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 57456873N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

An EtOAc (0.15 M) solution of N-cyclopropyl-3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzamide (1 eq.) from the previous step was eluted through an H-Cube hydrogenation apparatus equipped with a 10% palladium over carbon cartridge at a rate of 1 mL/min with EtOAc as the eluent. The hydrogenation was carried out using full hydrogen setting at RT. Purification of the crude product thus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customat RT
  2. customPurification of the crude product
  3. customthus obtained by way of flash chromatography (SiO2, 9:1 (v/v) Hex:EtOAc→EtOAc)

Sources & evidence

ORD record
ord-5d873036050443d2aebe67a162c2015a
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Linked notes

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