Toluene → HCID 21914386, compound

HRID 2421375Notes

Reaction equation

HRID 2421375 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Br[CH2:19][CH2:20][CH2:21][CH2:22]Br.C(N(C(C)C)CC)(C)C.C1(C)C=CC=CC=1>O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:4][C:3]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 80561,4-DibromobutaneHCID 81531DiisopropylethylamineHCID 21914489HCID 21914489, compound

Product 1

HCID 21914386HCID 21914386, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

4-Bromo-3-(2-{piperidin-1-yl}ethoxy)aniline (2.99 g), 1,4-dibromobutane (1.2 ml), diisopropylethylamine (4.18 ml) and toluene (15 ml) were stirred and heated at 110° C. for 18 h. When cool, water (20 ml) was added, and the mixture was extracted with ethyl acetate (2×30 ml). The combined organic phase was washed with water, brine, dried (MgSO4) and evaporated to give the product as an orange-brown oil (2.25 g).

Workup

  1. temperatureWhen cool
  2. extractionthe mixture was extracted with ethyl acetate (2×30 ml)
  3. washThe combined organic phase was washed with water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-9031e1297c0e449499bd5e7a4de7c68a
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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