N-(4-Hydroxyphenyl)glycine → HCID 68525824, compound

HRID 884078Notes

Reaction equation

HRID 884078 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[CH2:13]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[C:14]1[CH:22]=[CH:21][C:20]2[O:19][CH2:18][O:17][C:16]=2[CH:15]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.C(OCC)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]([N:26]2[CH2:27][CH2:28][N:23]([CH2:13][C:14]3[CH:22]=[CH:21][C:20]4[O:19][CH2:18][O:17][C:16]=4[CH:15]=3)[CH2:24][CH2:25]2)=[O:12])=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 67149N-(4-Hydroxyphenyl)glycineHCID 944261-PiperonylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 68525824HCID 68525824, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-hydroxyphenyl)glycine (11.38 g, 68.1 mmol) in N,N-dimethylformamide (DMF) (150 mL) were added under ice cooling 1-piperonylpiperazine (15.0 g, 68.1 mmol), 1-hydroxybenzotriazole monohydrate (10.43 g, 68.1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.66 g, 81.7 mmol), and the resulting solution was stirred for 30 minutes under ice cooling and for 4.5 hours at room temperature. The reaction solution was concentrated under reduced pressure. To the residue was added a saturated sodium bicarbonate solution (400 mL), and extracted with ethyl acetate (400 mL). The ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and evaporated, to leave the resulting product solidified in a powdered form. Ethyl acetate was added, and the resulting product was filtered off and washed with ethyl acetate, to thereby yield 18.58 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue was added a saturated sodium bicarbonate solution (400 mL)
  3. extractionextracted with ethyl acetate (400 mL)
  4. washThe ethyl acetate layer was washed with a saturated sodium bicarbonate solution and brine
  5. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customto leave the resulting product
  8. filtrationthe resulting product was filtered off
  9. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-9fe937e30fcc451b8a1981d2d0317ede
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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