Pyridine → HCID 12052639, compound

HRID 1264080Notes

Reaction equation

HRID 1264080 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15]3[C:16]([NH2:21])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.N1C=CC=CC=1.[N:30]1([CH2:35][CH2:36][O:37][C:38]2[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=2)[CH2:34][CH2:33][CH2:32][CH2:31]1.C(Cl)(Cl)Cl>ClCCl.CO>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:23]=[CH:22][C:12]([CH2:13][NH:14][C:15]3[C:16]([NH:21][C:42](=[O:43])[C:41]4[CH:40]=[CH:39][C:38]([O:37][CH2:36][CH2:35][N:30]5[CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:46][CH:45]=4)=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 12052627HCID 12052627, compoundHCID 120526284-[2-(1-Pyrrolidinyl)ethoxy]benzoyl chloride

Product 1

HCID 12052639HCID 12052639, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N1-[4-[2-(1-pyrrolidinyl)ethoxy]-benzyl]-1,2-benzenediamine (220 mg, 0.706 mmol) in dry dichloromethane (2 mL) was added pyridine (0.114 mL, 1.41 mmol, 2.0 eq.). To the resulting solution was added a suspension of 4-[2-(1-pyrrolidinyl)ethoxy]benzoyl chloride (179 mg, 0.706 mmol, 1.0 eq.) in dry dichloromethane (3 mL), portionwise, at 0° C., following the reaction by tlc (9:1 CHCl3:MeOH, 1% TEA). Once the aniline had been consumed, the reaction was allowed to warm to ambient temperature. The reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (15 mL) then diluted with ethyl acetate (60 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (15 mL), water (15 mL), brine (15 mL), dried over MgSO4, filtered then the solvent was removed under reduced pressure. The desired product was obtained after flash chromatography (eluting with 20:1 CHCl3:MeOH, 0.5% TEA) as a brown foam (361 mg, 97%).

Workup

  1. additionTo the resulting solution was added
  2. customat 0° C.
  3. customOnce the aniline had been consumed
  4. customThe reaction was quenched by the addition of saturated aqueous sodium bicarbonate solution (15 mL)
  5. additionthen diluted with ethyl acetate (60 mL)
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate (15 mL), water (15 mL), brine (15 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c7d4377dc6784ff294cfce48e9bb072f
Source dataset
uspto-grants-2003_04
Patent number
US06541499B1

Reaction notes

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