1-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzene → HCID 23501703, compound

HRID 2228532Notes

Reaction equation

HRID 2228532 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[C:12]([CH2:21][CH3:22])=[CH:11][C:10]=1[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH2:21]([C:12]1[C:13]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])=[CH:14][C:9]([OH:8])=[C:10]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH:11]=1)[CH3:22]

Participants

5

Reactant 2

HCID 235017961-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 23501703HCID 23501703, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask was charged with 10% palladium on carbon (200 mg), ethanol (20 mL), and 1-benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzene (500 mg). The flask was fitted with a balloon and pressurized with hydrogen to fully inflate the balloon. The reaction was stirred 3.5 hours, filtered through Celite, and the filtrate concentrated under vacuum to afford 4-ethyl-2-(4-fluorophenyl)-5-[(4-aminobutyl)oxy]phenol as a white powder (350 mg). HPLC showed that ˜25% starting material remained. It was not purified but carried directly into the next step. Mass Spec (EI), m/e=304.1 (M+H).

Workup

  1. customThe flask was fitted with a balloon
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record
ord-d62452c896db4086adfc7d2eb46f5350
Source dataset
uspto-grants-2002_07
Patent number
US06416733B1

Reaction notes

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