HCID 59750583, compound → 2-[4-(4-Aminobutyl)phenoxy]-N-[3-(dimethylamino)propyl]acetamide

HRID 747884Notes

Reaction equation

HRID 747884 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23](=[O:31])[NH:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[CH:17][CH:16]=1)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]([NH:24][CH2:25][CH2:26][CH2:27][N:28]([CH3:30])[CH3:29])=[O:31])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 59750583HCID 59750583, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 597505552-[4-(4-Aminobutyl)phenoxy]-N-[3-(dimethylamino)propyl]acetamideYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3 (377 mg, 0.85 mmol) and 10% palladium on carbon (0.30 g, 50% wet) in methanol (15 mL) was stirred at room temperature for 2 h under atmospheric pressure of hydrogen. The mixture was then filtered through a Celite pad and the solvent was evaporated to provide 4 (208 mg, 80%) as a white solid. The crude product was directly used in the next step without purification. 1H NMR (300 MHz, CD3OD) δ 1.61 (m, 6H), 2.11 (s, 6H), 2.32 (m, 2H), 2.65 (m, 4H), 3.28 (m, 2H), 4.45 (s, 2H), 6.90 (d, 2H), 7.19 (d, 2H). m/z (ESI) 308.

Workup

  1. filtrationThe mixture was then filtered through a Celite pad
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-de5c652747b54804b41283f466763412
Source dataset
uspto-grants-2008_07
Patent number
US07399766B2

Reaction notes

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