Diethyl Sulfate → 4-[[3-(p-Chlorophenyl)propyl]ethylamino]benzoic acid, ethyl ester

HRID 1154356Notes

Reaction equation

HRID 1154356 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.S(OCC)(O[CH2:27][CH3:28])(=O)=O.[OH-].[Na+]>ClCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][N:11]([CH2:27][CH3:28])[C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:21][CH:22]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6163Diethyl SulfateHCID 14798Sodium HydroxideHCID 13079692Ethyl 4-{[3-(4-chlorophenyl)propyl]amino}benzoate

Product 1

HCID 442788674-[[3-(p-Chlorophenyl)propyl]ethylamino]benzoic acid, ethyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1 g. of ethyl 4-[3-(p-chlorophenyl)propylamino]benzoate and 2.37 g. of diethyl sulfate is stirred at 130° C. for 3 hours. The mixture is then diluted with 10 ml. of dichloromethane and 10 ml. of water and adjusted to pH 11 with 10N sodium hydroxide. The dichloromethane layer is drawn off and saved. The aqueous layer is extracted with two 10 ml. portions of dichloromethane. The organic layers are combined, washed with 10 ml. of water, dried over anhydrous magnesium sulfate and evaported to an oil. This oil is chromatographed on a silica gel column, eluting with chloroform:hexane (1:3) giving a colorless liquid which is distilled, giving the desired product as a liquid, boiling point 160° C. (14 mm.).

Workup

  1. additionA mixture of 1 g
  2. additionThe mixture is then diluted with 10 ml
  3. extractionThe aqueous layer is extracted with two 10 ml
  4. washwashed with 10 ml
  5. dry with materialof water, dried over anhydrous magnesium sulfate
  6. customThis oil is chromatographed on a silica gel column
  7. washeluting with chloroform:hexane (1:3)
  8. customgiving a colorless liquid which
  9. distillationis distilled

Sources & evidence

ORD record
ord-3b72c3e564e1473398f67e4dfa2fa718
Source dataset
uspto-grants-1984_12
Patent number
US04489094

Reaction notes

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