Water → (3-Nitro-benzyl)dipropylamine

HRID 1759199Notes

Reaction equation

HRID 1759199 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Cl)([O-:3])=[O:2].[CH2:12]([NH:15][CH2:16][CH2:17][CH3:18])[CH2:13][CH3:14].O>C1C=CC=CC=1>[CH2:12]([N:15]([CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:16][CH2:17][CH3:18])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 8902DipropylamineHCID 12078alpha-Chloro-m-nitrotoluene

Product 1

HCID 13022589(3-Nitro-benzyl)dipropylamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5.13 g of m-nitro-benzyl chloride in 100 ml benzene at 10° C. was added in small portions 6.2 g of dipropylamine over a period of 15 minutes. The reaction mixture was stirred and allowed to come to room temperature for 1.5 hours, and was then refluxed for 4 hours. Water was added to the solution and the organic layer was separated and collected. The organic layer was washed with water (3×100 ml), dried (MgSO4) and stripped to leave a dark-red oil. The product (Compound No. 1) was chromatographed over silica gel (hexane: CH2Cl2 ; 1.0:0; 4:1), to yield the title product as a yellow-amber oil. Analysis: C: calculated, 66.08; found, 65.38. H: calculated, 8.53; found 8.55. N: calculated, 11.85; found, 11.73.

Workup

  1. temperaturewas then refluxed for 4 hours
  2. customthe organic layer was separated
  3. customcollected
  4. washThe organic layer was washed with water (3×100 ml)
  5. dry with materialdried (MgSO4)
  6. customto leave a dark-red oil
  7. customThe product (Compound No. 1) was chromatographed over silica gel (hexane: CH2Cl2 ; 1.0:0; 4:1)

Sources & evidence

ORD record
ord-d800e62ba88e4adaad1b3b2fdb7f8f55
Source dataset
uspto-grants-1982_07
Patent number
US04339461

Reaction notes

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