Benzylamine → HCID 23045306, compound

HRID 2108124Notes

Reaction equation

HRID 2108124 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(OCC)(=O)C>[O:12]([CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 23045281HCID 23045281, compound

Product 1

HCID 23045306HCID 23045306, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[3-[2-(3-Bromopropoxy)ethoxy]propoxy]benzene (1.6 g) was added dropwise with stirring to benzylamine (2.70 g) at 130° under nitrogen. The solution was stirred at 130° under nitrogen for 2 h, cooled and diluted with ethyl acetate (150 ml), and washed with 2N hydrochloric acid (100 ml). The aqueous phase was re-extracted with ethyl acetate (2×100 ml) and the combined organic phases washed with 8% sodium bicarbonate solution (150 ml), dried and evaporated in vacuo to give the title compound (1.21 g) as an oil. T.l.c. (System E 40:10:1) Rf 0.52

Workup

  1. temperaturecooled
  2. washwashed with 2N hydrochloric acid (100 ml)
  3. extractionThe aqueous phase was re-extracted with ethyl acetate (2×100 ml)
  4. washthe combined organic phases washed with 8% sodium bicarbonate solution (150 ml)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-50734639988543a09bc611b4972a2c09
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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