Triethylamine → 4-(Dimethylamino)-2-({methyl[2-(4-nitrophenyl)ethyl]amino}methyl)phenol

HRID 459740Notes

Reaction equation

HRID 459740 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH:10]=1)[CH:8]=O.Cl.[CH3:14][NH:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C.[BH4-].[Na+]>CO>[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[CH:5][C:6]([OH:11])=[C:7]([CH2:8][N:15]([CH3:14])[CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)[CH:10]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 4311764Sodium borohydrideHCID 129346465-(Dimethylamino)-2-hydroxybenzaldehydeHCID 16218354N-methyl-4-nitrophenethylamine hydrochloride

Product 1

HCID 98805464-(Dimethylamino)-2-({methyl[2-(4-nitrophenyl)ethyl]amino}methyl)phenolYield 34%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g (3 mmol) of 5-(dimethylamino)-2-hydroxybenzaldehyde (Bull. Chem. Soc. Jpn. (1978), 51 (8), 2433–2434) and 0.72 g (3.33 mmol) of N-methyl2-(4-nitrophenyl)ethylamine hydrochloride are placed in solution in 30 ml of anhydrous methanol under an inert atmosphere in the presence of 0.65 ml of triethylamine (4.5 mmol). The reaction mixture is stirred vigorously for 18 hours before the addition, by portions, of 126 mg (3.33 mmol) of NaBH4. Stirring is maintained for a further 4 hours before adding 10 ml of ice-cold water. The reaction mixture is extracted twice with 50 ml of CH2Cl2. The organic phase is washed with 10 ml of water, dried over sodium sulphate, filtered and concentrated under vacuum. The residue is purified on a silica column (eluent: CH2Cl2/MeOH: 97/3). The expected product is obtained in the form of a brown oil with a yield of 34% (0.34 g).

Workup

  1. temperatureis maintained for a further 4 hours
  2. extractionThe reaction mixture is extracted twice with 50 ml of CH2Cl2
  3. washThe organic phase is washed with 10 ml of water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified on a silica column (eluent: CH2Cl2/MeOH: 97/3)

Sources & evidence

ORD record
ord-8bfa9b63a2664afa8e754e4225e87d3c
Source dataset
uspto-grants-2007_03
Patent number
US07196084B2

Reaction notes

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