3-Hydroxybenzaldehyde → 3-[[[3-(4-Methoxyphenoxy)propyl]amino]methyl]phenol

HRID 1712173Notes

Reaction equation

HRID 1712173 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH2:9][CH2:10][NH2:11])=[CH:5][CH:4]=1.[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.O.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([O:7][CH2:8][CH2:9][CH2:10][NH:11][CH2:18][C:17]2[CH:20]=[CH:21][CH:22]=[C:15]([OH:14])[CH:16]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1013-HydroxybenzaldehydeHCID 962Water3×HCID 31521093-(4-Methoxy-phenoxy)-propylamineHCID 4311764Sodium borohydride

Product 1

HCID 231239643-[[[3-(4-Methoxyphenoxy)propyl]amino]methyl]phenol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3-(4-Methoxyphenoxy)propylamine (10.0 g) was dissolved in methanol (50 mL) at room temperature, a solution of 3-hydroxybenzaldehyde (6.7 g) in methanol (50 mL) was added dropwise within 5 minutes at water temperature (about 20° C.), and then the resulting mixture was stirred at room temperature for 20 hours. Then, sodium borohydride (2.1 g)/water (100 mL) was added dropwise at water temperature (about 20° C.) for 5 minutes, and the mixture was stirred at room temperature for 12 hours. Precipitates were removed, washed with water and then dried under reduced pressure at 80° C. for 5 hours. Pale yellow crystals were obtained (13.9 g, 87.4%).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. customPrecipitates
  3. customwere removed
  4. washwashed with water
  5. customdried under reduced pressure at 80° C. for 5 hours
  6. customPale yellow crystals were obtained (13.9 g, 87.4%)

Sources & evidence

ORD record
ord-86cf2e89ee1c48308415d4f0f71eabb0
Source dataset
uspto-grants-2010_09
Patent number
US07790903B2

Reaction notes

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