Phosphate → HCID 10822170, compound

HRID 981514Notes

Reaction equation

HRID 981514 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][NH2:9].P([O-])([O-])([O-])=[O:11].[C:15]1(C)C=[CH:19][CH:18]=[CH:17][CH:16]=1>CCOCC>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][CH2:8][N:9]1[CH2:15][CH2:16][CH2:17][CH2:18][C:19]1=[O:11]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 1140Toluene2×HCID 5650581-methyl-1H-pyrrole-2-ethylamine3×

Product 1

HCID 10822170HCID 10822170, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(1-Methylpyrrol-2-yl)ethylamine (4.96g, 0.04m) and triethylamine (5.6mL, 0.04m) were stirred together in toluene (60mL). A solution of ethyl 5-bromopentanoate (7.80g, 0.04m) in toluene (20 mL) was added dropwise over 1 hr at room temperature. The reaction mixture was heated with stirring at 70 degrees overnight. The reaction was worked up by addition of a phosphate buffer until a pH of 5-6 was reached; the reaction mixture was then diluted with ether and the layers were separated. The aqueous layer was exhaustively washed with diethyl ether. The combined organic layers were washed with water, brine and then dried over anhydrous potassium carbonate. The dryinq agent was filtered away, and the filtrate was concentrated to a light yellow solid weighing 5.2g. It was recrystallized from methylene chloride/hexane to give 4.2g (51.2%) of purified title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. customthe layers were separated
  3. washThe aqueous layer was exhaustively washed with diethyl ether
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationThe dryinq agent was filtered away
  7. concentrationthe filtrate was concentrated to a light yellow solid
  8. customIt was recrystallized from methylene chloride/hexane
  9. customto give 4.2g (51.2%)
  10. customof purified title compound

Sources & evidence

ORD record
ord-8d021f9f9d584a2f8410ed5b73af9cd1
Source dataset
uspto-grants-1991_02
Patent number
US04992441

Reaction notes

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