Triethylamine → HCID 54029509, compound

HRID 1460260Notes

Reaction equation

HRID 1460260 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]([C:40]2[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=2)([C:33]2[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=2)[OH:32])[CH2:27][CH2:26]1>CN(C)C=O>[CH2:12]([O:11][C:9](=[O:10])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][CH:28]([C:31]([C:40]3[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=3)([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[OH:32])[CH2:27][CH2:26]2)=[CH:7][CH:6]=1)[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 225219p-Aminophenylacetic acid ethyl esterHCID 19983145HCID 19983145, compound

Product 1

HCID 54029509HCID 54029509, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.18 g (0.02 mole) of ethyl p-nitrophenylacetate in 200 mL of ethanol is subjected to catalytic hydrogenation. The mixture is filtered to remove the catalyst and the filtrate is concentrated to obtain quantitative yield of ethyl 4-aminophenylacetate. To an agitated solution of the ethyl 4-aminophenylacetate and 2.02 g (0.02 mole) of triethylamine in 50 ml of dimethylformamide is added dropwise a solution of 7.58 g (0.020 mole) of 1-(3-chloropropyl)-α,α-bis(4-fluorophenyl)-4-piperidinemethanol in 20 ml of dimethylformamide. After stirring at ambient temperature for 4 hr the reaction mixture is heated at 70° C. for 4 hr. The reaction mixture is concentrated and the crude product partitioned between methylene chloride and water. The methylene chloride solution is washed with water, dried over anhydrous magnesium sulfate, and concentrated to yield the title compound.

Workup

  1. temperatureis heated at 70° C. for 4 hr
  2. concentrationThe reaction mixture is concentrated
  3. customthe crude product partitioned between methylene chloride and water
  4. washThe methylene chloride solution is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef97636c5c754503ba11e2054b38becd
Source dataset
uspto-grants-1991_12
Patent number
US05070087

Reaction notes

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