4-Hydroxybenzaldehyde → 4-(Phenethylaminomethyl)phenol

HRID 130808Notes

Reaction equation

HRID 130808 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([NH2:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[CH2:10]([NH:18][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([OH:1])=[CH:3][CH:4]=1)[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 1001PhenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 30425764-(Phenethylaminomethyl)phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 4-hydroxybenzaldehyde (1.00 g, 8.12 mmol) in methanol (40.6 mL). Add 3 Å molecular sieves and phenethylamine (1.02 mL, 8.12 mmol). Stir at room temperature for 17 hours. Add NaBH4 (0.341 g, 9.01 mmol). After five hours, filter and concentrate. Purify by 10 g SCX column washing with methanol and eluting with 2.0 M NH3 in methanol to give the title compound as an off white solid: HRMS calcd for C15H18NO 228.1388 (M+H)+, found 228.1387, time 0.74 min, MS TOF ES+ 228.1 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=1.4 min, 100% purity.

Workup

  1. waitAfter five hours
  2. filtrationfilter
  3. concentrationconcentrate
  4. customPurify by 10 g SCX column
  5. washwashing with methanol
  6. washeluting with 2.0 M NH3 in methanol

Sources & evidence

ORD record
ord-c8638e60c33b4cfc81226a0b142bed0a
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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