Acetic Acid → Ethyl [4-(2-heptyloxy-4-iodobenzylamino)phenyl]acetate

HRID 1171433Notes

Reaction equation

HRID 1171433 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)[CH3:2].C(O)(=O)C.[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:27]=1[CH:28]=O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C([BH3-])#N.[Na+]>CN(C=O)C>[CH2:18]([O:25][C:26]1[CH:33]=[C:32]([I:34])[CH:31]=[CH:30][C:27]=1[CH2:28][NH:12][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:11][CH:10]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 225219p-Aminophenylacetic acid ethyl esterHCID 5003444Sodium cyanoborohydrideHCID 860544942-Heptyloxy-4-iodobenzaldehyde

Product 1

HCID 86611168Ethyl [4-(2-heptyloxy-4-iodobenzylamino)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of ethyl(4-aminophenyl)acetate (1.76 g, 9.84 mmol) and acetic acid (0.71 ml) in DMF (71 ml) is added to a solution of 2-heptyloxy-4-iodobenzaldehyde of Step c (3.1 g, 8.94 mmol), acetic acid (0.71 ml) in DMF (71 ml). The mixture is stirred for 12 hours and then 1.12 g of sodium cyanoborohydride (17.89 mmol) is added. The mixture is heated at 60° C. for 4 hours. The desired product is extracted by addition of ethyl ether. The organic phase is washed with brine and then with water, dried with magnesium sulfate and concentrated using a rotary evaporator. The product is purified by chromatography on a silica column, eluted with a heptane/ethyl acetate 9:1 mixture. After evaporation of the solvents, 4.11 g (96%) of the expected compound are recovered in the form of a yellow oil.

Workup

  1. extractionThe desired product is extracted by addition of ethyl ether
  2. washThe organic phase is washed with brine
  3. dry with materialwith water, dried with magnesium sulfate
  4. concentrationconcentrated
  5. customa rotary evaporator
  6. customThe product is purified by chromatography on a silica column
  7. washeluted with a heptane/ethyl acetate 9:1 mixture
  8. customAfter evaporation of the solvents, 4.11 g (96%) of the expected compound
  9. customare recovered in the form of a yellow oil

Sources & evidence

ORD record
ord-c237a69320cb49e78451cc3a2c64184b
Source dataset
uspto-grants-2010_11
Patent number
US07829588B2

Reaction notes

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