4-Aminophenol hydrochloride → 4-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenol

HRID 1280911Notes

Reaction equation

HRID 1280911 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH:10]=O)[CH2:2][CH2:3][CH3:4].Cl.[NH2:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.C([BH3-])#N.[Na+]>CO>[CH2:1]([C:5]1[O:6][C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]=1[CH2:10][NH:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 58284-Aminophenol hydrochlorideHCID 49619662-Butyl-1-benzofuran-3-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 234456414-[(2-Butyl-benzofuran-3-ylmethyl)-amino]-phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At ambient temperature, to a stirred solution containing 2-n-butylbenzofuran-3-carboxaldehyde (0.888 g, 4.77 mmol) and 4-aminophenol hydrochloride in MeOH (7 mL) was added sodium cyanoborohydride (0.330 g, 5.25 mmol). After 24 h, the reaction was carefully quenched with 3N HCl, diluted with H2O and extracted with CH2Cl2. The organic extracts were washed with sat. aq. NaHCO3, dried and concentrated. Purification on silica gel eluting with a 20 & 40% EtOAc/pet. ether step gradient gave the title compound as a pale yellow solid. 1H NMR (CDCl3) δ 0.93 (t, 3H), 1.38 (sextet, 2H), 1.70 (quintet, 2H), 2.79 (t, 2H), 4.27 (s, 1H), 4.35 (br. s, 1H), 6.62 (d, 2H), 6.75 (d, 2H), 7.18-7.26 (m, 3H), 7.41 (d, 1H), 7.54 (d, 1H).

Workup

  1. customthe reaction was carefully quenched with 3N HCl
  2. additiondiluted with H2O
  3. extractionextracted with CH2Cl2
  4. washThe organic extracts were washed with sat. aq. NaHCO3
  5. customdried
  6. concentrationconcentrated
  7. customPurification on silica gel eluting with a 20 & 40% EtOAc/pet. ether step gradient

Sources & evidence

ORD record
ord-b4254d0d3c7d41308f97e7e5d42d0d7a
Source dataset
uspto-grants-2002_09
Patent number
US06451845B1

Reaction notes

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