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

HRID 1067350Notes

Reaction equation

HRID 1067350 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) δ0.93 (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-81676f01ca37441795454e767e42d5ab
Source dataset
uspto-grants-2001_06
Patent number
US06248764B1

Reaction notes

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