3-Hydroxybenzaldehyde → HCID 21071620, compound

HRID 1666863Notes

Reaction equation

HRID 1666863 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1.[OH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O.[BH4-].[Na+].O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][CH2:15][C:14]2[CH:17]=[CH:18][CH:19]=[C:12]([OH:11])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962WaterHCID 1393813-ChlorophenethylamineHCID 4311764Sodium borohydride

Product 1

HCID 21071620HCID 21071620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 2-(3-chlorophenyl)ethylamine (1.866 gm; 15.28 mmol) and 3-hydroxybenzaldehyde (1.567 gm; 10.07 mmol) in 40 mL of methanol and stir at room temperature for 20 min and treat with sodium borohydride (0.950 gm; 25.1 mmol) in one portion. Stir the mixture at room temperature. After 15 h, add water (10 mL), and remove the methanol by rotary evaporation. Add to this slurry water (25 mL) and dichloromethane (50 mL), separate the layers and extract the aqueous layer with dichloromethane (50 mL). Wash the combined organic layers with saturated brine (3×), dry over MgSO4, and concentrate to give the title compound.

Workup

  1. customremove the methanol
  2. customby rotary evaporation
  3. additionAdd to this slurry water (25 mL) and dichloromethane (50 mL)
  4. customseparate the layers
  5. extractionextract the aqueous layer with dichloromethane (50 mL)
  6. washWash the combined organic layers with saturated brine (3×)
  7. dry with materialdry over MgSO4
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-2a15d2ab68ed4b84907b556e9874f2a0
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Reaction notes

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