Acetic Acid → 4-(1,4-Dioxapent-1-yl)phenylbutylamine

HRID 81308Notes

Reaction equation

HRID 81308 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19](OCCOC)=[CH:18][CH:17]=1)(OCC1C=CC=CC=1)=O.[C:27](O)(=[O:29])C.[H][H].[CH2:33]([OH:35])[CH3:34]>[Pd]>[O:35]([CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:14][CH2:13][CH2:12][NH2:11])[CH2:33][CH2:34][O:29][CH3:27]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 22566171N-Cbz-4-[4-(1,4-Dioxapent-1-yl)phenyl]butylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 673657464-(1,4-Dioxapent-1-yl)phenylbutylamineYield 92%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 64 (2.27 g, 6.4 mmol) in ethanol (60 mL) with acetic acid (1 wt. %) was added Pd/C catalyst (300 mg, 10% wet) then the mixture was shaken for 18 h at 30 psi of hydrogen in a Parr hydrogenator. The pressure was released and the catalyst was filtered off through a pad of silica gel. The solvent was removed at reduced pressure to provide 65 (1.3 g, 92%). 1H NMR (300 MHz, CDCl3) δ 1.60 (br s, 4H), 2.00 (s, 2H) 2.55 (br s, 2H), 2.85 (br s, 2H), 3.47 (s, 3H), 3.73 (m, 2H), 4.10 (m, 2H), 6.82 (d, 2H), 7.08 (d, 2H).

Workup

  1. filtrationthe catalyst was filtered off through a pad of silica gel
  2. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-b8a51d3165ab402897cbd274deeba25c
Source dataset
uspto-grants-2014_09
Patent number
US08846688B2

Reaction notes

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