Acetic Anhydride → N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

HRID 1260500Notes

Reaction equation

HRID 1260500 reaction equation
[NH2:1][CH:2]([CH3:12])[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(OCC)(=O)C>[OH:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH:2]([NH:1][C:20](=[O:22])[CH3:21])[CH3:12])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 97939244-(3-Aminobutyl)phenol

Product 1

HCID 59956161N-[3-(4-Hydroxyphenyl)-1-methylpropyl]acetamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(3-Aminobutyl)phenol (510 mg, 3.087 mmol) and triethylamine (1.3 ml, 9.26 mmol) were dissolved in 30 ml of ethyl acetate. At 0° C., acetic anhydride (029 ml, 3.087 mmol) was added. The cooling bath was removed after 1 h. The reaction mixture was concentrated, and the residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA). Yield: 472 mg (74%) of N-[3-(4-hydroxyphenyl)-1-methylpropyl]acetamide, M+H+: 208.14 and 54 mg (7%) of 4-(3-acetylaminobutyl)phenyl acetate, M+H+: 250.13.

Workup

  1. customThe cooling bath was removed after 1 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by preparative HPLC (PR18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-7de699da68554f92a8a384ee3436799f
Source dataset
uspto-grants-2013_06
Patent number
US08470841B2

Reaction notes

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