Benzylamine → HCID 23045285, compound

HRID 2108125Notes

Reaction equation

HRID 2108125 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(OCC)(=O)C>[C:12]1([CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][NH:25][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 23045316HCID 23045316, compound

Product 1

HCID 23045285HCID 23045285, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[3-[2-(3-Bromopropoxy)ethoxy]propyl]benzene (3.01 g) was added dropwise over 5 min to benzylamine (5.35 g) at 120° under nitrogen. The solution was stirred at 130° for 4.5 h, cooled, diluted with ethyl acetate (200 ml) and washed with 2N hydrochloric acid (150 ml). The aqueous phase was re-extracted with ethyl acetate (2×100 ml) and the combined organic phases washed with 8% sodium bicarbonate solution (200 ml), dried and evaporated in vacuo to give the title compound (2.58 g) as an oil. T.l.c. (System E 40:10:1) Rf 0.49

Workup

  1. temperaturecooled
  2. washwashed with 2N hydrochloric acid (150 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 (200 ml)
  5. customdried
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5467efca8be5400dbab20523f7aa75f2
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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